Effective tuning of the arene and alkanesulfinamides for highly enantioselective synthesis of (S)-4-chlorophenylphenylmethylamine, a key intermediate for antihistamic (S)-cetirizine

被引：46

作者：

Han, ZX ^{[1
]}

Krishnamurthy, D ^{[1
]}

Grover, P ^{[1
]}

Fang, QK ^{[1
]}

Pflum, DA ^{[1
]}

Senanayake, CH ^{[1
]}

机构：

[1] Sepracor Inc, Chem Proc Res & Dev, Marlborough, MA 01752 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 22期

关键词：

D O I：

10.1016/S0040-4039(03)00903-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High diastereoselectivity (>94%) has been achieved in the phenylMgBr addition process to chlorophenyl aldimine derived from the new and sterically hindered triisopropylbenzene sulfinamide (TIPBSA) in the synthesis of a key intermediate of (S)-Cetirizine. Surprisingly, under the same reaction conditions, toluenesulfinamide derived chlorophenyl aldimine provided only 10% ee. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4195 / 4197

页数：3

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