Sequential perfluoroalkylation and asymmetric reduction of nitriles triggered with perfluoroalkyl titanates: catalytic asymmetric synthesis of perfluoroalkyl amines

被引：22

作者：

Mikami, Koichi ^{[1
]}

Murase, Tatsushi ^{[1
]}

Zhai, Lili ^{[1
]}

Kawauchi, Susumu ^{[1
]}

Itoh, Yoshimitsu ^{[1
]}

Ito, Shigekazu ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 10期

关键词：

N-ARYL IMINES; ENANTIOSELECTIVE HYDROGENATION; SELF-DISPROPORTIONATION; CRYSTAL-STRUCTURES; REAGENTS; LIGANDS; TRIFLUOROMETHYLATION; KETONES; ACID; BOND;

D O I：

10.1016/j.tetlet.2009.12.140

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantio-enriched perfluoroalkyl amines are shown to be synthesized by perfluororalkylation and asymmetric reduction of nitriles. Perfluoroalkylation of nitriles can be attained by the Lewis acidic perfluoroalkyl titanate reagents to give acyclic ketimines. Catalytic asymmetric hydrogenation of the acyclic ketimines affords the perfluoroalkyl amine products in up to 93% ee. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1371 / 1373

页数：3

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