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
收藏
页码：10361 / 10378
页数：18
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