N-PENTENYL GLYCOSIDES AS MEDIATORS IN THE ASYMMETRIC-SYNTHESIS OF MONOSUBSTITUTED CHIRAL NONRACEMIC TETRAHYDROFURANS AND GAMMA-LACTONES

被引:24
作者
LLERA, JM [1 ]
LOPEZ, JC [1 ]
FRASERREID, B [1 ]
机构
[1] DUKE UNIV,DEPT CHEM,PAUL M GROSS CHEM LAB,DURHAM,NC 27706
关键词
D O I
10.1021/jo00297a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Pentenyl glycosides can be oxidatively hy-drolyzed by treatment with N-bromosuccinimide, previous work having been focused on the usefulness of the resulting glycosyl moiety. In this paper, attention is focused on asymmetric induction in the 2-(bromomethyl)furan that is liberated. The enantiomeric excess depends strongly on the orientations at the anomeric centers and at C2, as well as on the protecting group on the C2 oxygen. a-Anomers display higher asymmetric induction, and rationalization of this observation is based on the assumption that the molecule reacts from the favored ground-state orientation, wherein the exo anomeric effect is displayed. The usefulness of this route to optically active furans has been probed by a synthesis of an insect pheromone from the Bledius species. © 1990, American Chemical Society. All rights reserved.
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页码:2997 / 2998
页数:2
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