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Last update: 26 Mar 2021

Publications

Recent research highlights can be found here.

• 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., 142, 47, 20247, 2020 (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, accepted (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, accepted (DOI: 10.1002/chem.202003392)

• Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents

  Yafei Guo, Syuzanna R. Harutyunyan

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

• Catalytic enantioselective addition of organometallics to unprotected carboxylic acids

  Xingchen Yan, Syuzanna R. Harutyunyan

  Nature Communications, 10, 3402, 2019 (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., 58, 12950, 2019 (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., 848, 4932-4939, 2019 (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, 51(05), 1253-1262, 2019 (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, 72, 642, 2018 (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., 57, 13547, 2018 (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, 3900, 2018 (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, 19, 561, 2018 (DOI: 10.1002/cphc.201701335)

• Highly enantioselective catalytic synthesis of chiral pyridines

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

  Nature Communications, 8, 2058, 2017 (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.139, 14224, 2017 (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., 56, 3041, 2017 (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, 12, 493, 2017 (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, 7, 13780, 2016 (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, 352, 433, 2016 (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, 18, 3065, 2016 (DOI: 10.1002/ejoc.201600493)

• 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), Springer, Heidelberg, 2015 (DOI: 10.1007/3418_2015_164)

• 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, 6, 1952, 2016 (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, 1247, 2016 (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., 22, 3558, 2016 (DOI: 10.1002/chem.201503412)

• Tertiary α-diarylmethylamines derived from diarylketimines and organomagnesium reagents

  Alaric Desmarchelier, Pablo Ortiz, Syuzanna R. Harutyunyan

  Chem. Commun., 51, 703, 2015 (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., 54, 3038, 2015 (DOI: 10.1002/anie.201409815)

• Catalytic asymmetric alkylation of Aryl Heteroaryl Ketones

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

  EurJOC, 2015, 72, 2015 (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., 20, 14250, 2014 (DOI: 10.1002/chem.201404458)

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

  Antonio Rizzo, Syuzanna R. Harutyunyan

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

• PROFILE: Early Excellence in Physical Organic Chemistry

  Syuzanna R. Harutyunyan

  Physical Organic Chemistry, 27, 629, 2014 (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, 356 (9), 2061, 2014 (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., 4, 1997, 2014 (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, 575, 2013 (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, 24(18): 2419, 2013 (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. 49 (48), 5450-5452, 2013 (DOI: 10.1039/C3CC41892H)

• Light on the horizon? Catalytic enantioselective photoreactions

  Aike Nijland, Syuzanna R. Harutyunyan

  Catal. Sci. Technol., 3 (5), 1180-1189, 2013 (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., 10, e21-e27, 2013 (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. 8, 11880-11883, 2012 (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., 51, 3164-3167, 2012 (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., 48, 1478-1480, 2012 (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, 10, 2878-2884, 2012 (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., 51, 1-5, 2012 (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., 48, 1748-1750, 2012 (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, 479, 208, 2011 (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 3, 377, 2011 (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 3, 53, 2010 (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.108, 2824, 2008 (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) 105, 8507, 2008 (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. 3747, 2008 (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. 47, 398, 2007 (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. 128, 9103, 2006 (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. 127, 9966, 2005 (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. 44, 2752, 2005 (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. 126, 12784, 2004 (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) 101, 5834, 2004 (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, John Wiley & Sons, Chap. 9.1, pp. 169, 2004 (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, part III, 132, 2004 (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. 1836, 2004 (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. 126, 9318, 2004 (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. 125, 12860, 2003 (DOI: 10.1021/ja035465e)

• A highly efficient ruthenium catalyst for metathesis reactions

  K. Grela, S. Harutyunyan, A. Michrowska

  Angew. Chem. Int. Ed. 41, 4038, 2002 (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. 8, 4633, 2002

• 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. 40, 1948, 2001 (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 12, 481, 2001 (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, 9, 1543, 2001 (DOI: 10.1002/chin.200223032)