Cinchona Alkaloids in Asymmetric
Organocatalysis

Tommaso Marcelli; Henk Hiemstra

doi:10.1055/s-0029-1218699

REVIEW

Cinchona Alkaloids in Asymmetric Organocatalysis

Tommaso Marcelli*^a, Henk Hiemstra*^b
^a Dipartimento di Chimica, Materiali ed Ingegneria Chimica ‘Giulio Natta’, Politecnico di Milano , Via Mancinelli 7, 20131 Milano, Italy
Fax: +39(02)23993080; e-Mail: tommaso.marcelli@chem.polimi.it;
^b Van ‘t Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
Fax: +31(20)5255604; e-Mail: h.hiemstra@uva.nl ;

Abstract

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Abstract

This article reviews the applications of cinchona alkaloids as asymmetric catalysts. In the last few years, characterized by the resurgence of interest in asymmetric organocatalysis, cinchona derivatives have been shown to catalyze an outstanding array of chemical reactions, often with remarkable stereoselectivity. This work presents an overview of the transformations developed in the period from 2001 through 2009, highlighting applications in the synthesis of bioactive molecules and natural products.

1 Introduction

2 Additions to Carbonyls

3 Additions to Imines

4 Conjugate Additions

5 Additions to Olefins

6 Nucleophilic Substitutions

7 Electrophilic Halogenations

8 Opening of Cyclic Anhydrides

9 Acylations

10 Cycloadditions

11 Rearrangements

12 Decarboxylations

13 Miscellaneous

14 Conclusions and Outlook

List of abbreviations: Alloc, allyloxycarbonyl; Boc, tert-butyloxycarbonyl; Bs, benzenesulfonyl; BTTP, tert-butyliminotri(pyrrolidino)phosphorane; Cbz, benzyloxycarbonyl; DABCO, 1,4-diazabicyclo[2.2.2]octane; DBAD, dibenzyl azodicarboxylate; DBU, 1,8-diazabicycloundec-7-ene; DCE, 1,2-dichloroethane; DFT, density functional theory; DIPEA, N,N-diisopropylethylamine; DNP, 2,4-dinitrophenyl; DMB, 3,4-dimethoxybenzoyl; DPM, diphenylmethyl; DTAD, di-tert-butyl azodicarboxylate; EVE, ethyl vinyl ether; EWG, electron-withdrawing group; FBSM, 1-fluorobis(phenylsulfonyl)methane; HFiPA, 1,1,1,3,3,3-hexafluoro-2-propyl acrylate; LAH, lithium aluminum hydride; LG, leaving group; Moc, methyloxycarbonyl; MPEG, poly(ethylene glycol) monomethyl ether; MS, molecular sieves; MVK, methyl vinyl ketone; NFSI, N-fluorobenzenesulfonimide; NMR, nuclear magnetic resonance; Ns, p-nitrophenylsulfonyl; PEG, poly(ethylene glycol); PS, proton sponge [1,8-bis(dimethylamino)naphthalene]; rds, rate-determining step; TBAF, tetrabutylammonium fluoride; TCCA, trichloroisocyanuric acid; TFAA, trifluoroacetic anhydride; THF, tetrahydrofuran; TMAF, tetramethylammonium fluoride; TMS, trimethylsilyl; Ts, p-toluenesulfonyl; UNCA, urethane-protected α-amino acid N-carboxyanhydrides.

Key words

cinchona alkaloids - organocatalysis - asymmetric catalysis - kinetic resolution - stereoselective synthesis

Full Text

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<A NAME="RE26109SS-83">83</A> Song J. Wang Y. Deng L. J. Am. Chem. Soc. 2006, 128: 6048

<A NAME="RE26109SS-84">84</A> Bode CA. Ting A. Schaus SE. Tetrahedron 2006, 62: 11499

<A NAME="RE26109SS-85">85</A> Tillman AL. Ye JX. Dixon DJ. Chem. Commun. 2006, 1191

<A NAME="RE26109SS-86A">86a</A> Ting A. Lou S. Schaus SE. Org. Lett. 2006, 8: 2003

<A NAME="RE26109SS-86B">86b</A> Lou S. Dai P. Schaus SE. J. Org. Chem. 2007, 72: 9998

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<A NAME="RE26109SS-88">88</A> Song J. Shih HW. Deng L. Org. Lett. 2007, 9: 603

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<A NAME="RE26109SS-92A">92a</A> Fortner KC. Shair MD. J. Am. Chem. Soc. 2007, 129: 1032

<A NAME="RE26109SS-92B">92b</A> Magdziak D. Lalic G. Lee HM. Fortner KC. Aloise AD. Shair MD. J. Am. Chem. Soc. 2005, 127: 7284

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Ref. 41.

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<A NAME="RE26109SS-204">204</A> Li HM. Song J. Liu XF. Deng L. J. Am. Chem. Soc. 2005, 127: 8948

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<A NAME="RE26109SS-209A">209a</A> Liu XF. Li HM. Deng L. Org. Lett. 2005, 7: 167

<A NAME="RE26109SS-209B">209b</A> Liu X. Sun B. Deng L. Synlett 2009, 1685

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<A NAME="RE26109SS-211A">211a</A> Brandes S. Bella M. Kjoersgaard A. Jørgensen KA. Angew. Chem. Int. Ed. 2006, 45: 1147

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<A NAME="RE26109SS-217">217</A> Lygo B. To DCM. Chem. Commun. 2002, 2360

<A NAME="RE26109SS-218A">218a</A> Ye JX. Wang YC. Liu RH. Zhang GF. Zhang Q. Chen JP. Liang XM. Chem. Commun. 2003, 2714

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<A NAME="RE26109SS-220">220</A> Jew S. Lee JH. Jeong BS. Yoo MS. Kim MJ. Lee YJ. Lee J. Choi SH. Lee K. Lah MS. Park H. Angew. Chem. Int. Ed. 2005, 44: 1383

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<A NAME="RE26109SS-226">226</A> Fioravanti S. Mascia MG. Pellacani L. Tardella PA. Tetrahedron 2004, 60: 8073

<A NAME="RE26109SS-227">227</A> For a review, see: Pellissier H. Tetrahedron 2008, 64: 7041

<A NAME="RE26109SS-228A">228a</A> Papageorgiou CD. Ley SV. Gaunt MJ. Angew. Chem. Int. Ed. 2003, 42: 828

<A NAME="RE26109SS-228B">228b</A> Papageorgiou CD. Dios MACD. Ley SV. Gaunt MJ. Angew. Chem. Int. Ed. 2004, 43: 4641

<A NAME="RE26109SS-229A">229a</A> Bremeyer N. Smith SC. Ley SV. Gaunt MJ. Angew. Chem. Int. Ed. 2004, 43: 2681

<A NAME="RE26109SS-229B">229b</A> Johansson CCC. Bremeyer N. Ley SV. Owen DR. Smith SC. Gaunt MJ. Angew. Chem. Int. Ed. 2006, 45: 6024

<A NAME="RE26109SS-230">230</A> Kojima S. Suzuki M. Watanabe A. Ohkata K. Tetrahedron Lett. 2006, 47: 9061

<A NAME="RE26109SS-231A">231a</A> Jew SS. Jeong BS. Yoo MS. Huh H. Park HG. Chem. Commun. 2001, 1244

<A NAME="RE26109SS-231B">231b</A> Park HG. Jeong BS. Yoo MS. Park MK. Huh H. Jew SS. Tetrahedron Lett. 2001, 42: 4645

<A NAME="RE26109SS-231C">231c</A> Park HG. Jeong BS. Yoo MS. Lee JH. Park MK. Lee YJ. Kim MJ. Jew SS. Angew. Chem. Int. Ed. 2002, 41: 3036

<A NAME="RE26109SS-231D">231d</A> Park HG. Jeong BS. Yoo MS. Lee JH. Park BS. Kim MG. Jew SS. Tetrahedron Lett. 2003, 44: 3497

<A NAME="RE26109SS-231E">231e</A> Lee JH. Yoo MS. Jung JH. Jew SS. Park HG. Jeong BS. Tetrahedron 2007, 63: 7906

<A NAME="RE26109SS-232A">232a</A> Jew SS. Yoo MS. Jeong BS. Park IY. Park HG. Org. Lett. 2002, 4: 4245

<A NAME="RE26109SS-232B">232b</A> Yoo MS. Jeong BS. Lee JH. Park HG. Jew SS. Org. Lett. 2005, 7: 1129

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<A NAME="RE26109SS-235">235</A> For an account, see: Lygo B. Beaumont DJ. Chimia 2007, 61: 257

<A NAME="RE26109SS-236A">236a</A> Lygo B. Crosby J. Lowdon TR. Wainwright PG. Tetrahedron 2001, 57: 2391

<A NAME="RE26109SS-236B">236b</A> Lygo B. Crosby J. Lowdon TR. Peterson JA. Wainwright PG. Tetrahedron 2001, 57: 2403

<A NAME="RE26109SS-236C">236c</A> Lygo B. Allbutt B. Synlett 2004, 326

<A NAME="RE26109SS-236D">236d</A> Lygo B. Andrews BI. Hirst JD. Melville JL. Peterson JA. Slack D. Chim. Oggi - Chem. Today 2004, 22: 8

<A NAME="RE26109SS-237A">237a</A> Lygo B. Crosby J. Peterson JA. Tetrahedron 2001, 57: 6447

<A NAME="RE26109SS-237B">237b</A> Lygo B. Humphreys LD. Tetrahedron Lett. 2002, 43: 6677

<A NAME="RE26109SS-238">238</A> Lemaire C. Gillet S. Guillouet SP. Plenevaux A. Aerts JL. Luxen A. Eur. J. Org. Chem. 2004, 2899

<A NAME="RE26109SS-239">239</A> Elango S. Venugopal M. Suresh PS. Tetrahedron 2005, 61: 1443

<A NAME="RE26109SS-240">240</A> Kumar S. Ramachandran U. Tetrahedron 2005, 61: 7022

<A NAME="RE26109SS-241">241</A> Li Q. Li L. Pei W. Wang S. Zhang Z. Synth. Commun. 2008, 38: 1470

<A NAME="RE26109SS-242">242</A> Bozkurt S. Durmaz M. Yilmaz M. Sirit A. Tetrahedron: Asymmetry 2008, 19: 618

<A NAME="RE26109SS-243A">243a</A> Chinchilla R. Mazon P. Najera C. Tetrahedron: Asymmetry 2002, 13: 927

<A NAME="RE26109SS-243B">243b</A> Chinchilla R. Mazon P. Najera C. Ortega FJ. Tetrahedron: Asymmetry 2004, 15: 2603

<A NAME="RE26109SS-244A">244a</A> Siva A. Murugan E. Synthesis 2005, 2927

<A NAME="RE26109SS-244B">244b</A> Siva A. Murugan E. J. Mol. Catal. A: Chem. 2005, 241: 111

<A NAME="RE26109SS-244C">244c</A> Siva A. Murugan E. J. Mol. Catal. A: Chem. 2006, 248: 1

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<A NAME="RE26109SS-249">249</A> Mase N. Ohno T. Morimoto H. Nitta F. Yoda H. Takabe K. Tetrahedron Lett. 2005, 46: 3213

<A NAME="RE26109SS-250A">250a</A> Thierry B. Perrard T. Audouard C. Plaquevent JC. Cahard D. Synthesis 2001, 1742

<A NAME="RE26109SS-250B">250b</A> Thierry B. Plaquevent JC. Cahard D. Tetrahedron: Asymmetry 2001, 12: 983

<A NAME="RE26109SS-250C">250c</A> Thierry B. Plaquevent JC. Cahard D. Tetrahedron: Asymmetry 2003, 14: 1671

<A NAME="RE26109SS-251">251</A> Wang X. Yin L. Yang T. Wang YM. Tetrahedron: Asymmetry 2007, 18: 108

<A NAME="RE26109SS-252">252</A> Danelli T. Annunziata R. Benaglia M. Cinquini M. Cozzi F. Tocco G. Tetrahedron: Asymmetry 2003, 14: 461

<A NAME="RE26109SS-253A">253a</A> Shi Q. Lee Y. Song H. Cheng M. Jew S. Park H. Jeong B. Chem. Lett. 2008, 37: 436

<A NAME="RE26109SS-253B">253b</A> Shi QH. Lee YJ. Kim MJ. Park NK. Lee KY. Song HR. Cheng MS. Jeong BS. Park HG. Jew SS. Tetrahedron Lett. 2008, 49: 1380

<A NAME="RE26109SS-254A">254a</A> Chinchilla R. Mazon P. Najera C. Adv. Synth. Catal. 2004, 346: 1186

<A NAME="RE26109SS-254B">254b</A> Chinchilla R. Mazon P. Najera C. Molecules 2004, 9: 349

<A NAME="RE26109SS-255">255</A> Patterson DE. Xie SP. Jones LA. Osterhout MH. Henry CG. Roper TD. Org. Process Res. Dev. 2007, 11: 624

<A NAME="RE26109SS-256A">256a</A> Gong JH. Kim HR. Ryu EK. Kim JN. Bull. Korean Chem. Soc. 2002, 23: 789

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<A NAME="RE26109SS-256C">256c</A> Cho C.-W. Krische MJ. Angew. Chem. Int. Ed. 2004, 43: 6689

<A NAME="RE26109SS-256D">256d</A> Cho C.-W. Kong J.-R. Krische MJ. Org. Lett. 2004, 6: 1337

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<A NAME="RE26109SS-259">259</A> Du Y. Han X. Lu X. Tetrahedron Lett. 2004, 45: 4967

<A NAME="RE26109SS-260">260</A> Van Steenis D. Marcelli T. Lutz M. Spek AL. Van Maarseveen JH. Hiemstra H. Adv. Synth. Catal. 2007, 349: 281

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<A NAME="RE26109SS-263B">263b</A> Bell M. Poulsen TB. Jørgensen KA. J. Org. Chem. 2007, 72: 3053

<A NAME="RE26109SS-263C">263c</A> Poulsen T. Dickmeiss G. Overgaard J. Jørgensen K. Angew. Chem. Int. Ed. 2008, 47: 4687

<A NAME="RE26109SS-264A">264a</A> Bella M. Kobbelgaard S. Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 3670

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<A NAME="RE26109SS-265B">265b</A> France S. Weatherwax A. Lectka T. Eur. J. Org. Chem. 2005, 475

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<A NAME="RE26109SS-268B">268b</A> Baudequin C. Plaquevent JC. Audouard C. Cahard D. Green Chem. 2002, 4: 584

<A NAME="RE26109SS-268C">268c</A> Baudequin C. Loubassou JF. Plaquevent JC. Cahard D. J. Fluorine Chem. 2003, 122: 189

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