In:
European Journal of Organic Chemistry, Wiley, Vol. 2007, No. 33 ( 2007-11), p. 5492-5495
Abstract:
The highly enantioselective organocatalytic β‐hydroxylation of α,β‐unsaturated ketones was accomplished by using oximes as the oxygen‐centered nucleophile. Optically active products are obtained with enantioselectivity up to 94 %. Central to these studies was the use of catalytic primary amine salt A , in which both the cation and the anion are chiral. Amine A exhibits high reactivity and selectivity for iminium‐ion catalysis with enones. The potential interest of this novel transformation was demonstrated with the easy conversion of the Michael adducts in enantioenriched anti and syn 1,2‐diols without erosion of the optical purity.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2007:33
DOI:
10.1002/ejoc.200700873
Language:
English
Publisher:
Wiley
Publication Date:
2007
detail.hit.zdb_id:
1475010-7