Publications

Asymmetric Nucleophilic Addition to Ketones and Ketimines and Conjugate Addition Reactions

Luo Ge and Syuzanna R. Harutyunyan

Catalytic Asymmetric Synthesis, Fourth Edition; Takahiko Akiyama, Iwao Ojima, 2022, John Wiley & Sons, Inc., Chap. 16, 617. (DOI: 10.1002/9781119736424.ch16)

Cu(I)-Catalyzed Alkynylation of Quinolones

Aitor Maestro, Sebastien Lemaire, and Syuzanna R. Harutyunyan

Org. Lett., 2022, Accepted Manuscript (DOI: 10.1021/acs.orglett.2c00020)

Manganese (I)-Catalyzed Access to 1,2-Bisphosphine Ligands

Luo Ge and Syuzanna R Harutyunyan

Chem. Sci., 2022, 13, 1307–1312 (DOI: 10.1039/D1SC06694C)

Manganese(I)-Catalyzed H–P Bond Activation via Metal–Ligand Cooperation

Juana M. Pérez, Roxana Postolache, Marta Castiñeira Reis, Esther G. Sinnema, Denisa Vargová, Folkert de Vries, Edwin Otten, Luo Ge, and Syuzanna R. Harutyunyan

J. Am. Chem. Soc., 2021, 143, 48, 20071–20076 (DOI: 10.1021/jacs.1c10756)

Pd-catalyzed allylative dearomatisation using Grignard reagents

Cosimo Boldrini, Syuzanna R. Harutyunyan

Chem. Commun., 2021, 57, 11807 (DOI: 10.1039/D1CC05609C)

Enantioselective Catalytic Dearomative Addition of Grignard Reagents to 4-Methoxypyridinium Ions

Yafei Guo, Marta Castiñeira Reis, Johanan Kootstra, Syuzanna R. Harutyunyan

ACS Catal., 2021, 11, 14, 8476–8483 (DOI: 10.1021/acscatal.1c01544)

Nucleophilic Dearomatization of N-Heteroaromatics Enabled by Lewis Acids and Copper Catalysis

Xingchen Yan, Luo Ge, Marta Castiñeira Reis, and Syuzanna R. Harutyunyan

J. Am. Chem. Soc., 2020, 142, 47, 20247 (DOI: 10.1021/jacs.0c09974)

Highlighted in the November 2020 Spotlights on Recent JACS Publications

Copper Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines

Luo Ge, Mercedes Zurro, Syuzanna R. Harutyunyan

Chem. Eur. J., 2020, 26, 16277 (DOI: 10.1002/chem.202004232)

Lewis acid promoted dearomatization of naphthols

Kirill Kulish, Cosimo Boldrini, Marta Castiñeira Reis, Juana Pérez, Syuzanna R. Harutyunyan

Chem. Eur. J., 2020, 26, 15843 (DOI: 10.1002/chem.202003392)

Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents

Yafei Guo, Syuzanna R. Harutyunyan

Beilstein J. Org. Chem., 2020, 16, 1006 (DOI: 10.3762/bjoc.16.90)

Catalytic enantioselective addition of organometallics to unprotected carboxylic acids

Xingchen Yan, Syuzanna R. Harutyunyan

Nature Communications, 2019, 10, 3402 (DOI: 10.1038/s41467-019-11345-z)

Highly enantioselective catalytic addition of Grignard reagents to N‐heterocyclic acceptors

Yafei Guo, Syuzanna R. Harutyunyan

Angew. Chem. Int. Ed., 2019, 58, 12950 (DOI: 10.1002/anie.201906237)

Highlighted in Synfacts 2019, 10, 1141

Ring-Closing Metathesis on Commercial Scale: Synthesis of HCV Protease Inhibitor Simeprevir

András Horváth, Dominique Depré, Wim A. A. Vermeulen, Stijn L. Wuyts, Syuzanna R. Harutyunyan, Grégori Binot, Jef Cuypers, Wouter Couck, Dirk Van Den Heuvel

J. Org. Chem., 2019, 848, 4932 (DOI: 10.1021/acs.joc.8b03124)

Lewis Acid Promoted Trapping of Chiral Aza-enolates

Francesco Lanza, Juana M. Pérez Galera, Ravindra P. Jumde, Syuzanna R. Harutyunyan

Synthesis, 2019, 51(05), 1253 (DOI: 10.1055/s-0037-1611657)

Synergistic Action of Copper Catalysts and Lewis Acids in Carbon-Carbon Bond Forming Reactions

Manas Das, Syuzanna R. Harutyunyan

Chimia, 2018, 72, 642 (DOI: 10.2533/chimia.2018.642)

Catalytic regio- and enantioselective alkylation of conjugated dienyl amides

Yafei Guo, Johanan Kootstra, Syuzanna R. Harutyunyan

Angew. Chem. Int. Ed., 2018, 57, 13547 (DOI: 10.1002/anie.201808392)

Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes

Juan F. Collados, Pablo Ortiz, Juana M. Pérez,Yafei Xia, Mark A. J. Koenis, Wybren J. Buma, Valentin P. Nicu, Syuzanna R. Harutyunyan

EurJOC, 2018, 2018, 3900 (DOI: 10.1002/ejoc.201701469)

Regional susceptibility in VCD spectra to dynamic molecular motions: the case of a benzyl α-hydroxysilane

Yafei Xia, Mark Koenis, Juan F. Collados, Pablo Ortiz, Syuzanna R. Harutyunyan, Lucas Visscher, Wybren J. Buma

ChemPhysChem, 2018, 19, 561 (DOI: 10.1002/cphc.201701335)

Highly enantioselective catalytic synthesis of chiral pyridines

Ravindra P. Jumde, Francesco Lanza, Tilde Pellegrini, Syuzanna R. Harutyunyan

Nature Communications, 2017, 8, 2058 (DOI: 10.1038/s41467-017-01966-7)

Lewis Acid Enabled Copper-Catalyzed Asymmetric Synthesis of Chiral β-Substituted Amides

Mamen Rodríguez-Fernández, Xingchen Yan, Juan F. Collados, Paul B. White, Syuzanna R. Harutyunyan

J. Am. Chem. Soc., 2017, 139, 14224 (DOI: 10.1021/jacs.7b07344)

Copper catalysed enantioselective alkylation of enolizable ketimines with organomagnesium reagents

Pablo Ortiz, Juan F. Collados, Ravindra P. Jumde, Edwin Otten, Syuzanna R. Harutyunyan

Angew. Chem. Int. Ed., 2017, 56, 3041 (DOI: 10.1002/anie.201609963)

Cu-catalyzed enantioselective allylic alkylation with organolithium reagents

Valentín Hornillos, Sureshbabu Guduguntla, Martín Fañanás-Mastral, Manuel Pérez, Pieter H. Bos, Alena Rudolph, Syuzanna R. Harutyunyan, Ben L. Feringa

Nature Protocols, 2017, 12, 493 (DOI: 10.1038/nprot.2016.179)

Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines

Jiawei Rong, Juan F. Collados, Pablo Ortiz, Ravindra P. Jumde, Edwin Otten, Syuzanna R. Harutyunyan

Nature Communications, 2016, 7, 13780 (DOI: 10.1038/ncomms13780)

Catalytic asymmetric addition of Grignard reagents to alkenyl-substituted aromatic N-heterocycles

Ravindra P. Jumde, Francesco Lanza, Marieke J. Veenstra, Syuzanna R. Harutyunyan

Science, 2016, 352, 433 (DOI: 10.1126/science.aaf1983)

Highlighted in Synform 2016/10, A148

On the Configurational Stability and Reactivity of Tertiary Silyloxy Carbanions Derived from Stereoselective Brook Rearrangement

Juan F. Collados, Pablo Ortiz, Syuzanna R. Harutyunyan

EurJOC, 2016, 18, 3065 (DOI: 10.1002/ejoc.201600493)

Catalytic Synthesis of Enantiopure Chiral Alcohols via Addition of Grignard Reagents to Carbonyl Compounds

Juan F. Collados, Ricard Solà, Syuzanna R. Harutyunyan, Beatriz Maciá

ACS Catalysis, 2016, 6, 1952 (DOI: 10.1021/acscatal.5b02832)

Direct synthesis of enolizable N-sulfonyl ketimines under microwave irradiation

Pablo Ortiz, Juan F. Collados, Syuzanna R. Harutyunyan

EurJOC, 2016, 2016, 1247 (DOI: 10.1002/ejoc.201600022)

Synthesis of chiral tertiary alcohols via Cu(I)-catalyzed enatioselective addition of organomagnesium reagents to ketones

Jiawei Rong, Tilde Pellegrini, Syuzanna R. Harutyunyan

Chem. Eur. J., 2016, 22, 3558 (DOI: 10.1002/chem.201503412)

1,2- Versus 1,4-Asymmetric Addition of Grignard Reagents to Carbonyl Compounds

Pablo Ortiz, Francesco Lanza, Syuzanna R. Harutyunyan

in "Topics in Organometallic Chemistry" (Ed.: S. R. Harutyunyan), 2015, Springer, Heidelberg (DOI: 10.1007/3418_2015_164)

Tertiary α-diarylmethylamines derived from diarylketimines and organomagnesium reagents

Alaric Desmarchelier, Pablo Ortiz, Syuzanna R. Harutyunyan

Chem. Commun., 2015, 51, 703 (DOI: 10.1039/C4CC06719C)

Catalytic Asymmetric Alkylation of Acylsilanes

Jiawei Rong, Rik Oost, Alaric Desmarchelier, Adriaan J. Minnaard, Syuzanna R. Harutyunyan

Angew. Chem. Int. Ed., 2015, 54, 3038 (DOI: 10.1002/anie.201409815)

Catalytic asymmetric alkylation of Aryl Heteroaryl Ketones

Pablo Ortiz, Ana Maria del Hoyo, Syuzanna R. Harutyunyan

EurJOC, 2015, 2015, 72 (DOI: 10.1002/ejoc.201403297)

Ischia Advanced School of Organic Chemistry 2014

Luca Bernardi, Syuzanna R. Harutyunyan

Chemistry Views, 2014,

Total synthesis of (R,R,R)-g-tocopherol through Cu-catalyzed asymmetric 1,2-addition

Zhongtao Wu, Syuzanna R. Harutyunyan, Adriaan J. Minnaard

Chem. Eur. J., 2014, 20, 14250 (DOI: 10.1002/chem.201404458)

Azabicycles Construction: the Transannular Ring Contraction with N-Protected Nucleophiles

Antonio Rizzo, Syuzanna R. Harutyunyan

Organic & Biomolecular Chemistry, 2014, 12, 6570 (DOI: 10.1039/C4OB01311E)

PROFILE: Early Excellence in Physical Organic Chemistry

Syuzanna R. Harutyunyan

Physical Organic Chemistry, 2014, 27, 629 (DOI: 10.1002/poc.3326)

Cu-catalyzed conjugate addition of Grignard reagents to 2-methyl cyclopentenone and sequential enolate alkylation

Beatriz C. Calvo, Ashoka V. R. Madduri, Syuzanna R. Harutyunyan, Adriaan J. Minnaard

Advanced Synthesis & Catalysis, 2014, 356 (9), 2061 (DOI: 10.1002/adsc.201400085)

Synthesis of new derivatives of copper complexes of Josiphos family ligands for applications in asymmetric catalysis

Rik Oost, Jiawei Rong, Adriaan J. Minnaard, Syuzanna R. Harutyunyan

Catal. Sci. Technol., 2014, 4, 1997 (DOI: 10.1039/C4CY00180J)

Catalytic Asymmetric Synthesis of Dihydrofurans and Cyclopentenols with Tertiary Stereocenters

Zhongtao Wu, Ashoka V. R. Madduri, Syuzanna R. Harutyunyan, Adriaan J. Minnaard

EurJOC, 2013, 2013, 575 (DOI: 10.1002/ejoc.201301476)

Structural Characterisation of Cu Complexes of Chiral Ferrocenyl Diphosphine Ligands

Francesca Caprioli, Martin Lutz, Auke Meetsma, Adriaan J. Minnaard, Syuzanna R. Harutyunyan

Synlett, 2013, 24(18): 2419 (DOI: 10.1055/s-0033-1339851)

Asymmetric Amplification in the Catalytic Enantioselective 1,2-Addition of Grignard Reagents to Enones

Francesca Caprioli, Ashoka V. R. Madduri, Adriaan J. Minnaard, Syuzanna R. Harutyunyan

Chem. Commun., 2013, 49 (48), 5450 (DOI: 10.1039/C3CC41892H)

Light on the horizon? Catalytic enantioselective photoreactions

Aike Nijland, Syuzanna R. Harutyunyan

Catal. Sci. Technol., 2013, 3 (5), 1180 (DOI: 10.1039/C3CY20858C)

Catalytic asymmetric alkylation of ketones using organometallic reagents

Ashoka V. Maduri, Syuzanna R. Harutyunyan, Adriaan J. Minnaard

Drug Discov Today: Technol., 2013, 10, e21-e27 (DOI: 10.1016/j.ddtec.2012.10.010)

Asymmetric Allylic Alkylation of Acyclic Allylic Ethers with Organolithium Reagents

Manuel Pérez, Martín Fañanás-Mastral, Valentín Hornillos, Alena Rudolph, Pieter H. Bos, Syuzanna R. Harutyunyan, Ben L. Feringa

Chem. Eur. J., 2012, 8, 11880 (DOI: 10.1002/chem.201202251)

Asymmetric Copper-Catalysed Addition of Grignard Reagents to Aryl Alkyl Ketones

Ashoka V. R. Madduri, Syuzanna R. Harutyunyan and Adriaan J. Minnaard

Angew. Chem. Int. Ed., 2012, 51, 3164-3167 (DOI: 10.1002/anie.201109040)

Copper(I) catalyzed asymmetric 1,2-addition of Grignard reagents to α-methyl substituted α,β-unsaturated ketones

Ashoka V. R. Madduri, Adriaan J. Minnaard and Syuzanna R. Harutyunyan

Chem. Comm., 2012, 48, 1478 (DOI: 10.1039/c1cc16725a)

Note: this paper is an invited contribution to the issue on Emerging Investigators

Access to Chiral α-Bromo and α-H-Substituted Tertiary Allylic Alcohols via Copper(I) Catalyzed 1,2-Addition of Grignard Reagents to Enones

Ashoka V. R. Madduri, Adriaan J. Minnaard and Syuzanna R. Harutyunyan

Org.Biomol.Chem., 2012, 10, 2878 (DOI: 10.1039/C2OB25080B)

Enantioselective Synthesis of Tertiary and Quaternary Stereogenic Centers: Copper/Phosphoramidite-Catalyzed Allylic Alkylation with Organolithium Reagents

Martín Fañanás-Mastral, Manuel Pérez, Pieter H. Bos, Alena Rudolph, Syuzanna R. Harutyunyan, and Ben L. Feringa

Angew. Chem. Int. Ed., 2012, 51, 1 (DOI: 10.1002/anie.201107840)

Highlighted in SYNFACTS

Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents

Pieter H. Bos, Alena Rudolph, Manuel Pérez, Martín Fañanás-Mastral, Syuzanna R. Harutyunyan and Ben L. Feringa

Chem. Comm., 2012, 48, 1748 (DOI: 10.1039/C2CC16855C)

Electrically driven directional motion of a four-wheeled molecule on a metal surface

T. Kudernac, N. Ruangsupapichat, M. Parschau, B. Maciá, N. Katsonis, S. R. Harutyunyan, K.-H. Ernst, B. L. Feringa

Nature, 2011, 479, 208 (DOI: 10.1038/nature10587)

Catalytic asymmetric carbon-carbon bond formation via allylic alkylations with organolithium compounds

M. Pérez, M. Fañanás-Mastral, P. H. Bos, A. Rudolph, S. R. Harutyunyan, B. L. Feringa

Nature Chemistry, 2011, 3, 377 (DOI: 10.1038/nchem.1009)

Highlighted in Nature, SYNFACTS and in C&E New

Reversing the direction in a light-driven rotary molecular motor

N. Ruangsupapichat, M. M. Pollard, S. R. Harutyunyan, B. L. Feringa

Nature Chemistry, 2010, 3, 53 (DOI: Highlighted in C&E News)

Catalytic Asymmetric Conjugate Addition and Allylic Alkylation with Grignard reagent

S. R. Harutyunyan, T. den Hartog, K. Geurts, A. J. Minnaard, B. L. Feringa

Chem. Rev., 2008, 108, 2824 (DOI: 10.1021/cr068424k)

Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis

S. R. Harutyunyan, T. den Hartog, A. J. Minnaard, B. L. Feringa

Proc. Natl. Acad. Sci. USA (PNAS), 2008, 105, 8507 (DOI: 10.1073/pnas.0709289105)

Manganese catalysed asymmetric cis-dihydroxylation with H2O2

J. W. de Boer, W. R. Browne, S. R. Harutyunyan, L. Bini, T. D. Tiemersma-Wegman, P. L. Alsters, R. Hage, B. L. Feringa

Chem. Commun., 2008, 32, 3747 (DOI: 10.1039/B808355J)

Catalytic enantioselective 1,6-conjugate addition of Grignard reagents to linear dienoates

T. den Hartog, S. R. Harutyunyan, D. Font, A. J. Minnaard, B. L. Feringa

Angew. Chem. Int. Ed., 2007, 47, 398 (DOI: 10.1002/anie.200703702)

On the Mechanism of the Copper-Catalyzed Enantioselective 1,4-Addition of Grignard Reagents to α,β-Unsaturated Carbonyl Compounds

S. R. Harutyunyan, F. López, W. R. Browne, A. Correa, D. Peña, R. Badorrey, A. Meetsma, A. J. Minnaard, B. L. Feringa

J. Am. Chem. Soc., 2006, 128, 9103 (DOI: 10.1021/ja0585634)

An Iterative Catalytic Route to Enantiopure Deoxypropionate Subunits: Asymmetric Conjugate Addition of Grignard Reagents to α,β-Unsaturated Thioesters

R. Des Mazery, M. Pullez, F. López, S. R. Harutyunyan, A. J. Minnaard, B. L. Feringa

J. Am. Chem. Soc., 2005, 127, 9966 (DOI: 10.1021/ja053020f)

Copper-catalyzed enantioselective conjugate addition of Grignard reagents to α,β-Unsaturated esters

F. López, S. R. Harutyunyan, A. Meetsma, A. J. Minnaard, B. L. Feringa

Angew. Chem. Int. Ed., 2005, 44, 2752 (DOI: 10.1002/anie.200500317)

Copper-Catalyzed Enantioselective Conjugate Addition of Grignard Reagents to Acyclic Enones

F. López, S. R. Harutyunyan, A. J. Minnaard, and B. L. Feringa

J. Am. Chem. Soc., 2004, 126, 12784 (DOI: 10.1021/ja046632t)

Copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones

B. L. Feringa, R. Badorrey, D. Peña, S. R. Harutyunyan, A. J. Minnaard

Proc. Natl. Acad. Sci. USA (PNAS), 2004, 101, 5834 (DOI: 10.1073/pnas.0308008101)

Olefin Metathesis Reactions

S. R. Harutyunyan, A. Michrowska, K. Grela, S. J. Connon, A. M. Dunne, S. Blechert, G. Bhaskar and B. Venkateswara Rao

in Catalysts for Fine Chemical Synthesis: Metal Catalysed Carbon-Carbon Bond-Forming Reactions, Volume 3, Ed.: S. M. Roberts, J. Xiao, J. Whittall, T. E. Pickett, 2004, , John Wiley & Sons, Chap. 9.1, pp. 169, (DOI: 10.1002/0470862017.ch9)

Nucleophilic addition to an achiral dehydroalanine Schiff base Ni(II) complex as a route to amino acids. A case of stereodetermining asymmetric protonation in the presence of TADDOL

Y. N. Belokon, S. R. Harutyunyan, E. V. Vorontsov, A. S. Peregudov, V. N. Chrustalev, K. A. Kochetkov, D. Pripadchev, A. S. Saghiyan, A. K. Beck, D. Seebach

ARKIVOC, 2004, part III, 132 (DOI: 10.3998/ark.5550190.0005.313)

Highly enantioselective Cu-catalyzed asymmetric 1,4-addition of diphenylzinc to cyclohexenone

D. Peña, S. R. Harutyunyan, A. J. Minnaard, B. L. Feringa

Chem. Comm., 2004, 16, 1836 (DOI: 10.1039/B402868F)

Nitro-Substituted Hoveyda-Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation

A. Michrowska, R. Bujok, S. Harutyunyan, V. Sashuk, G. Dolgonos, K. Grela

J. Am. Chem. Soc., 2004, 126, 9318 (DOI: 10.1021/ja048794v)

Synthesis of α-Amino Acids via Asymmetric Phase Transfer-Catalyzed Alkylation of Achiral Nickel(II) Complexes of Glycine-Derived Schiff Bases

Yu. N. Belokon, N. B. Bespalova, T. D. Churkina, M. G. Ezernitskaya, S. R. Harutyunyan, I. Císařová, H. B. Kagan, K. A. Kochetkov, P. Kočovský, O. V. Larionov, K. A. Lyssenko, S. Peregudov, V. V. Prisyazhnyuk, Š. Vyskočil, M. North

J. Am. Chem. Soc., 2003, 125, 12860 (DOI: 10.1021/ja035465e)

A highly efficient ruthenium catalyst for metathesis reactions

K. Grela, S. Harutyunyan, A. Michrowska

Angew. Chem. Int. Ed., 2002, 41, 4038 (DOI: 10.1002/1521-3757(20021104)114:213.0.CO;2-J)

2,8'- disubstituted-1,1'-binaphthyls: a new pattern in chiral ligands

Š. Vyskočil, L. Meca, I. Tislerova, I. Cisarova, M. Polasek, S. R. Harutyunyan, Y. N. Belokon, R. M. J. Stead, L. Farrugia, S. C. Lockhart, W. L. Mitchell, P. Kočovský

Chem. Eur. J., 2002, 8, 4633

Highly efficient catalytic synthesis of α-amino acids under phase-transfer conditions with a novel catalyst/substrate pair

Yu. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R Harutyunyan, M. Nort, S. Viscochil, H. B. Kagan

Angew. Chem. Int. Ed., 2001, 40, 1948 (DOI: 10.1002/1521-3773(20010518)40:103.0.CO;2-O)

A new synthesis of enantiomerically pure syn-(S)-β-hydroxy-α-amino acids via asymmetric aldol reactions of aldehydes with a homochiral Ni(II)-glycine/(S)-BPB Schiff base complex

Yu. N. Belokon, K. A. Kochetkov, N. S. Ikonnikov, T. V. Strelkova, S. R. Harutyunyan, A. S. Saghiyan

Tetrahedron: Asymmetry, 2001, 12, 481 (DOI: 10.1016/S0957-4166(01)00071-4)

Asymmetric Michael reaction of diethyl malonate with crotonaldehyde catalyzed by chiral aminocarboxylates, amino alcoholates, and amino phenolates

K. A. Kochetkov, S. R. Harutyunyan, N. A. Kuzmina, T. F. Saveleva,V. I. Maleev, A. S. Peregudov, S. Vyscochil, A. S. Saghiyan

Izv. Acad. Nauc, Ser. Khim, 2001, 9, 1543 (DOI: 10.1002/chin.200223032)