On the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals

被引：40

作者：

Baiget, Jessica ^{[1
]}

Cosp, Annabel ^{[1
]}

Galvez, Erik ^{[1
]}

Gomez-Pinal, Loreto ^{[1
]}

Romea, Pedro ^{[1
]}

Urpi, Felix ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Catalonia, Spain

来源：

TETRAHEDRON | 2008年 / 64卷 / 24期

关键词：

asymmetric synthesis; chiral auxiliaries; titanium enolates; acetals;

D O I：

10.1016/j.tet.2008.04.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Titanium enolates from chiral N-propanoyl-1,3-thiazolidine-2-thiones containing bulky substituents at C4 turned out to be excellent platforms to get highly stereocontrolled cross-coupling reactions with acetals. Related oxazolidinethiones also afforded good results, but the corresponding oxazolidinones resulted completely unselective for such reactions, which proves that an exocyclic C=S bond is essential to attain a synthetically useful stereocontrol. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5637 / 5644

页数：8

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