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. 2010 Feb 3;132(4):1226-7.
doi: 10.1021/ja909640b.

Copper(I)-catalyzed asymmetric monoborylation of 1,3-dienes: synthesis of enantioenriched cyclic homoallyl- and allylboronates

Yusuke Sasaki  1 , Chongmin Zhong, Masaya Sawamura, Hajime Ito
Affiliations

Copper(I)-catalyzed asymmetric monoborylation of 1,3-dienes: synthesis of enantioenriched cyclic homoallyl- and allylboronates

Yusuke Sasaki et al. J Am Chem Soc. .

Abstract

Copper(I)-catalyzed asymmetric monoborylation of 1,3-dienes has been developed. We describe the production of either optically active homoallyl- or allylboronates with high regio- and enantioselectivity (88-97% ee) through monoborylation of 1,3-dienes. The reaction with 1,3-cyclohexadiene derivatives afforded the corresponding enantioenriched homoallyboronates. By simply changing the reaction conditions, a drastic change of product preference between homoallyl- and allylboronates was found in the reaction of 1,3-cyclopentadiene and 1,3-cycloheptadiene.

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