Copper(I)-Secondary Diamine Complex-Catalyzed Enantioselective Conjugate Boration of Linear β,β-Disubstituted Enones

I-Hon Chen, Motomu Kanai and Masakatsu Shibasaki*

*Institute of Microbial Chemistry, Tokyo, Kamiosaki 3-14-23, Shinagawa-ku, Tokyo 141-0021, Japan, Email: mshibasabikaken.or.jp

I-H. Chen, M. Kanai, M. Shibasaki, Org. Lett., 2010, 12, 4098-4101.

DOI: 10.1021/ol101691p

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Abstract

A copper(I)-chiral secondary diamine complex catalyzes an enantioselective conjugate boration of β,β-disubstituted enones in high yields and up to 99% ee. The resulting chiral tertiary organoboronates can be converted to enantiomerically enriched β-hydroxy ketones without any racemization.

see article for more examples

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Catalytic Asymmetric Synthesis of Chiral Tertiary Organoboronic Esters through Conjugate Boration of β-Substituted Cyclic Enones

I-H. Chen, L. Yin, W. Itano, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2009, 131, 11284-11285.

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Key Words

Boration

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ID: J54-Y2010-2600