Stereodivergent synthesis of 1,4-bifunctional compounds by regio- and diastereoselective Pd-catalyzed allylic substitution reaction

被引：9

作者：

Maezaki, Naoyoshi ^{[1
]}

Yano, Masahiro ^{[1
]}

Hirose, Yuki ^{[1
]}

Itoh, Yoshikazu ^{[1
]}

Tanaka, Tetsuaki ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 44期

关键词：

catalytic reaction; 1,4-bifunctional compound; stereoselective reaction; 1,3-asymmetric transfer;

D O I：

10.1016/j.tet.2006.08.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly stereoselective synthesis of 1,4-bifunctional compounds was accomplished via 1,2-asymmetric induction to alpha-oxyaldehyde and alpha-oxyketone followed by regio- and diastereoselective Pd-catalyzed allylic substitution reaction. We found that trifluoroacetate is a suitable leaving group for the allylic substitution reaction. Various nucleophiles containing carbon, nitrogen, and sulfur can be applied to the method. Both 1,4-syn- and 1,4-anti-adducts were synthesized with high stereoselectivity by using stereodivergent reduction of the propargyl alcohols followed by allylic substitution reaction. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：10361 / 10378

页数：18

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