Construction of Quaternary Stereogenic Centers from Tertiary
Boronic Esters

doi:10.1055/s-0030-1260396

Synfacts 2011(6): 0625-0625
DOI: 10.1055/s-0030-1260396

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters

Contributor(s):Mark Lautens, Patrick T. Franke

R. P. Sonawane, V. Jheengut, C. Rabalakos, R. Larouche-Gauthier, H. K. Scott, V. K. Aggarwal*
University of Bristol, UK
Enantioselective Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters: Methodology and Applications
Angew. Chem. Int. Ed. 2011, 50: 3760-3763

Abstract

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Key words

borates - chirality - natural products - olefination - stereogenic centers

Significance

The authors report on a lithiation-borylation reaction with subsequent one-carbon homologation or vinylation. The ready availability of the starting materials, broad range of substrates, bearing versatile functional groups with quaternary stereogenic centers, and very high enantioselectivities are noteworthy.

Comment

This methodology allows the formation of quaternary stereogenic centers with high enantioselectivity. It should be mentioned that products can be obtained exhibiting contiguous quaternary and tertiary stereogenic centers with high diastereoselectivities.

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