STUDY OF THE REGIOSELECTIVITY AND ENANTIOSELECTIVITY OF THE REACTIONS OF OSMIUM-TETROXIDE WITH ALLYLIC ALCOHOLS AND ALLYLIC SULFONAMIDES

被引：45
|
作者：
XU, DQ [1 ]
PARK, CY [1 ]
SHARPLESS, KB [1 ]
机构：
[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 16期
关键词：
D O I：
10.1016/S0040-4039(00)77153-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regioselectivities of the osmylation of geraniol, its derivatives and geranyl sulfonamides suggest the presence of a moderate attractive interaction between OsO4 and the allylic groups bearing acidic protons. This allylic directing effect may be due to the development of a hydrogen bonding interaction between OsO4 and the substrates during the osmylation process. The potential for a hydrogen bond can also have a substantial effect on the enantioselectivities of the osmium tetroxide catalyzed asymmetric dihydroxylation of allylic alcohols.
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收藏
页码：2495 / 2498
页数：4
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