Recent Advances in Copper-catalyzed Asymmetric Coupling Reactions

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2016 Jan 7

PMID 26734106

Citations 6

Authors

Fengtao Zhou

Qian Cai

Affiliations

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Abstract

Copper-catalyzed (or -mediated) asymmetric coupling reactions have received significant attention over the past few years. Especially the coupling reactions of aryl or alkyl halides with nucleophiles became a very powerful tool for the formation of C-C, C-N, C-O and other carbon-heteroatom bonds as well as for the construction of heteroatom-containing ring systems. This review summarizes the recent progress in copper-catalyzed asymmetric coupling reactions for the formation of C-C and carbon-heteroatom bonds.

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References

Tanaka K, Suzuki H, Osuga H . Non-Photochemical Route to Chiral Disubstituted [7]Thiaheterohelicenes via Biaryl- and Carbonyl-Coupling Reactions. J Org Chem. 1997; 62(13):4465-4470. DOI: 10.1021/jo970272t. View

Fleming I, Barbero A, Walter D . Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds. Chem Rev. 2002; 97(6):2063-2192. DOI: 10.1021/cr941074u. View

Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M . Aryl-aryl bond formation one century after the discovery of the Ullmann reaction. Chem Rev. 2002; 102(5):1359-470. DOI: 10.1021/cr000664r. View

Michaud G, Bulliard M, Ricard L, Genet J, Marinetti A . A strategy for the stereoselective synthesis of unsymmetric atropisomeric ligands: preparation of NAPhePHOS, a new biaryl diphosphine. Chemistry. 2002; 8(15):3327-30. DOI: 10.1002/1521-3765(20020802)8:15<3327::AID-CHEM3327>3.0.CO;2-F. View

Ley S, Thomas A . Modern synthetic methods for copper-mediated C(aryl)[bond]O, C(aryl)[bond]N, and C(aryl)[bond]S bond formation. Angew Chem Int Ed Engl. 2003; 42(44):5400-49. DOI: 10.1002/anie.200300594. View

Qiu L, Wu J, Chan S, Au-Yeung T, Ji J, Guo R . Remarkably diastereoselective synthesis of a chiral biphenyl diphosphine ligand and its application in asymmetric hydrogenation. Proc Natl Acad Sci U S A. 2004; 101(16):5815-20. PMC: 395991. DOI: 10.1073/pnas.0307774101. View

Hoveyda A, Hird A, Kacprzynski M . Small peptides as ligands for catalytic asymmetric alkylations of olefins. Rational design of catalysts or of searches that lead to them?. Chem Commun (Camb). 2004; (16):1779-85. DOI: 10.1039/b401123f. View

Yorimitsu H, Oshima K . Recent progress in asymmetric allylic substitutions catalyzed by chiral copper complexes. Angew Chem Int Ed Engl. 2005; 44(29):4435-9. DOI: 10.1002/anie.200500653. View

Kreis M, Friedmann C, Brase S . Diastereoselective Hartwig-Buchwald reaction of chiral amines with rac-[2.2]paracyclophane derivatives. Chemistry. 2005; 11(24):7387-94. DOI: 10.1002/chem.200500386. View

10.

Ito H, Kawakami C, Sawamura M . Copper-catalyzed gamma-selective and stereospecific substitution reaction of allylic carbonates with diboron: efficient route to chiral allylboron compounds. J Am Chem Soc. 2005; 127(46):16034-5. DOI: 10.1021/ja056099x. View

11.

Gorobets E, McDonald R, Keay B . Diastereospecific intramolecular Ullmann couplings: unique chiral auxiliary for the preparation of 3,3'-disubstituted MeO-BIPHEP derivatives. Org Lett. 2006; 8(7):1483-5. DOI: 10.1021/ol060484p. View

12.

Xie X, Chen Y, Ma D . Enantioselective arylation of 2-methylacetoacetates catalyzed by CuI/trans-4-hydroxy-L-proline at low reaction temperatures. J Am Chem Soc. 2006; 128(50):16050-1. DOI: 10.1021/ja066991j. View

13.

Ito H, Ito S, Sasaki Y, Matsuura K, Sawamura M . Copper-catalyzed enantioselective substitution of allylic carbonates with diboron: an efficient route to optically active alpha-chiral allylboronates. J Am Chem Soc. 2007; 129(48):14856-7. DOI: 10.1021/ja076634o. View

14.

Alexakis A, Backvall J, Krause N, Pamies O, Dieguez M . Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions. Chem Rev. 2008; 108(8):2796-823. DOI: 10.1021/cr0683515. View

15.

Harutyunyan S, den Hartog T, Geurts K, Minnaard A, Feringa B . Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents. Chem Rev. 2008; 108(8):2824-52. DOI: 10.1021/cr068424k. View

16.

Evano G, Blanchard N, Toumi M . Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. Chem Rev. 2008; 108(8):3054-131. DOI: 10.1021/cr8002505. View

17.

Ma D, Cai Q . Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles. Acc Chem Res. 2008; 41(11):1450-60. DOI: 10.1021/ar8000298. View

18.

Takenaka K, Itoh N, Sasai H . Enantioselective synthesis of C2-symmetric spirobilactams via Pd-catalyzed intramolecular double N-arylation. Org Lett. 2009; 11(7):1483-6. DOI: 10.1021/ol900016g. View

19.

Monnier F, Taillefer M . Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions. Angew Chem Int Ed Engl. 2009; 48(38):6954-71. DOI: 10.1002/anie.200804497. View

20.

Matsubara R, Jamison T . Nickel-catalyzed allylic substitution of simple alkenes. J Am Chem Soc. 2010; 132(20):6880-1. PMC: 2893574. DOI: 10.1021/ja101186p. View