Highly anti-selective SN2′ substitutions of chiral cyclic 2-iodo-allylic alcohol derivatives with mixed zinc-copper reagents

被引：58

作者：

Calaza, MI ^{[1
]}

Hupe, E ^{[1
]}

Knochel, P ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 07期

关键词：

D O I：

10.1021/ol0340742

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Functionalized allylic electrophilic reagents such as chiral 2-iodo-1-cyclohexenyl and -cyclopentenyl phosphates undergo highly stereoselective ant S(N)2'-allylic substitution reactions with a wide range of organozinc reagents (R2Zn and RZnl) leading to chiral products with a transfer of the chiral information >95%. The use of functionalized organozinc iodides allows preparation of the bicyclic enones 8 and 9 in greater than or equal to93% ee.

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页码：1059 / 1061

页数：3

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