Diastereoselective Chloroallylboration of α-Chiral Aldehydes

Double asymmetric reaction of chiral (Z)-(γ-chloroallyl)borane, 2, with α-chiral aldehydes (3−7) provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins (8−17) and vinyl epoxides (18−27). Both enantiomers of 2 exhibited excellent diatereose...

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Bibliographic Details
Published in:Journal of organic chemistry 1998-11, Vol.63 (24), p.8843-8849
Main Authors: Hu, Shaojing, Jayaraman, Seetharaman, Oehlschlager, Allan C
Format: Article
Language:English
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Summary:Double asymmetric reaction of chiral (Z)-(γ-chloroallyl)borane, 2, with α-chiral aldehydes (3−7) provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins (8−17) and vinyl epoxides (18−27). Both enantiomers of 2 exhibited excellent diatereoselectivity (≥90 de) for matched cases. The mismatched cases yielded moderate to good diastereoselectivity.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo980977a