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. 2011 Dec 14;133(49):19598-601.
doi: 10.1021/ja207607s. Epub 2011 Nov 21.

Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes

Masayuki Wasa  1 , Keary M Engle, David W Lin, Eun Jeong Yoo, Jin-Quan Yu
Affiliations

Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes

Masayuki Wasa et al. J Am Chem Soc. .

Abstract

Systematic ligand development has led to the identification of novel mono-N-protected amino acid ligands for Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes. A diverse range of organoboron reagents can be used as coupling partners, and the reaction proceeds under mild conditions. These results provide a new retrosynthetic disconnection for the construction of enantioenriched cis-substituted cyclopropanecarboxylic acids.

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Figures

Scheme 1
Scheme 1
Desymmetrization of Prochiral C–H Bonds
Scheme 2
Scheme 2
Asymmetric Cyclopropane C–H Activation
See this image and copyright information in PMC

References

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    1. For recent examples of asymmetric Pd(0)-catalyzed C–H functionalization reactions using chiral phosphine or carbene ligands, see: Albicker MR, Cramer N. Angew Chem Int Ed. 2009;48:9139.Renaudat A, Jean-Gerard L, Jazzar R, Kefalidis CE, Clot E, Baudoin O. Angew Chem Int Ed. 2010;122:7419.Nakanishi M, Katayev D, Besnard C, Kündig EP. Angew Chem Int Ed. 2011;50:7438.Anas S, Cordi A, Kagan HB. Chem Commun. doi: 10.1039/c1cc14292e.

    1. For an example of Ru-catalyzed atropselective alkylation, see: Kakiuchi F, Le Gendre P, Yamada A, Ohtaki H, Murai S. Tetrahedron: Asymmetry. 2000;11:2647.

    1. For examples of C–H activation followed by enantioselective addition to olefins, see: Mikami K, Hatano M, Terada M. Chem Lett. 1999:55.Thalji RK, Ellman JA, Bergman RG. J Am Chem Soc. 2004;126:7192.

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