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Synfacts 2011(6): 0625-0625
DOI: 10.1055/s-0030-1260396
DOI: 10.1055/s-0030-1260396
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters
Contributor(s):Mark Lautens, Patrick T. FrankeR. 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
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
Further Information
Publication History
Publication Date:
19 May 2011 (online)
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.