Diastereoselective chloroallylboration of alpha-chiral aldehydes

Authors
Hu, SJ Jayaraman, S Oehlschlager, AC
Citation
Sj. Hu et al., Diastereoselective chloroallylboration of alpha-chiral aldehydes, J ORG CHEM, 63(24), 1998, pp. 8843-8849
Citations number
51
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
63
Issue
24
Year of publication
1998
Pages
8843 - 8849
Database
ISI
SICI code
0022-3263(19981127)63:24<8843:DCOAA>2.0.ZU;2-U
Abstract
Double asymmetric reaction of chiral (Z)-(gamma-chloroallyl)borane, 2, with alpha-chiral aldehydes (3-7) provide a new practical method for the genera tion of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins (8-1 7) and vinyl epoxides(18-27). Both enantiomers of 2 exhibited excellent dia tereoselectivity (greater than or equal to 90 de) for matched cases. The mi smatched cases yielded moderate to good diastereoselectivity.