The stereoselective addition of titanium(IV) enolates of 1,3-oxazolidin-2-one and 1,3-thiazolidine-2-thione to cyclic N-acyliminium ion.: The total synthesis of (+)-isoretronecanol

被引：19

作者：

Pereira, E

Alves, CD

Böckelmann, MA

Pilli, RA

机构：

[1] UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil

[2] Univ Estadual Oeste Parana, Toledo, PR, Brazil

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 15期

基金：

巴西圣保罗研究基金会;

关键词：

titanium(IV) enolates; 1,3-oxazolidin-2-one; 1,3-thiazolidine-2-thione; N-acyliminium ion; (+)-isoretronecanol;

D O I：

10.1016/j.tetlet.2005.02.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Isoretronecanol (1) has been prepared in four steps and 36% overall yield via the diastereoselective addition of the titanium(IV) enolate derived from N-4-chlorobutyryl-1,3-thiazolidine-2-thione (3) to N-Boc-2-methoxypyrrolidine (5), which afforded 2-substituted pyrrolidine 7 in 84% yield (8:1 diastereoisomeric ratio), followed by reductive recovery of the chiral auxiliary and cyclization. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2691 / 2693

页数：3

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