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Published September 1, 2010 | Accepted Version + Supplemental Material
Journal Article Open

Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins

Abstract

A method for asymmetric alkyl−alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with alkylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.

Additional Information

© 2010 American Chemical Society. Received July 5, 2010. We thank Angelika Bruckmann for preliminary studies. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM62871).

Attached Files

Accepted Version - nihms228431.pdf

Supplemental Material - ja105924f_si_001.pdf

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Created:
August 19, 2023
Modified:
October 20, 2023