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. 2007 Nov 22;9(24):5123-6.
doi: 10.1021/ol702425a. Epub 2007 Nov 2.

Highly versatile enantioselective conjugate addition of Grignard reagents to alpha,beta-unsaturated thioesters

Beatriz Maciá Ruiz  1 , Koen Geurts, M Angeles Fernández-Ibáñez, Bjorn ter Horst, Adriaan J Minnaard, Ben L Feringa
Affiliations

Highly versatile enantioselective conjugate addition of Grignard reagents to alpha,beta-unsaturated thioesters

Beatriz Maciá Ruiz et al. Org Lett. .

Abstract

Herein, we report efficient catalysts for the asymmetric copper-catalyzed conjugate addition of Grignard reagents to alpha,beta-unsaturated thioesters. MeMgBr adds to aromatic alpha,beta-unsaturated thioesters with excellent enantioselectivities and moderate to good yields using Josiphos/CuBr and Tol-BINAP/CuI complexes. The use of bulky Grignard reagents leads to unprecedented enantioselectivities in the 1,4-addition to a broad range of aromatic and aliphatic alpha,beta-unsaturated thioesters using Tol-BINAP/CuI. The highest enantioselectivities reported so far for the addition of Grignard reagents to crowded beta-substituted aliphatic substrates are achieved with Tol-BINAP/CuI.

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