Highly stereoselective anti SN2′ substitutions of (Z)-allylic pentafluorobenzoates with polyfunctionalized zinc-copper reagents

被引：109

作者：

Harrington-Frost, N ^{[1
]}

Leuser, H ^{[1
]}

Calaza, MI ^{[1
]}

Kneisel, FF ^{[1
]}

Knochel, P ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 12期

关键词：

D O I：

10.1021/ol034525i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Allylic substitution reactions of zinc-copper organometallics on (Z)-allylic pentafluorobenzoates proceed with very high regioselectivity and excellent anti selectivity. The high fidelity in transfer of stereochemical information allowed a short synthesis of (+)-ibuprofen (97% ee).

引用

页码：2111 / 2114

页数：4

共 64 条

[61] CHIRAL ARENETHIOLATOCOPPER(I) CATALYZED SUBSTITUTION-REACTIONS OF ACYCLIC ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS [J].