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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