A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines

被引：24

作者：

Dangerfield, Emma M. ^{[1
,2
]}

Gulab, Shivali A. ^{[3
]}

Plunkett, Catherine H. ^{[1
,2
]}

Timmer, Mattie S. M. ^{[1
]}

Stocker, Bridget L. ^{[2
]}

机构：

[1] Victoria Univ Wellington, Sch Chem & Phys Sci, Wellington, New Zealand

[2] Malaghan Inst Med Res, Wellington, New Zealand

[3] Ind Res Ltd, Lower Hutt, New Zealand

来源：

CARBOHYDRATE RESEARCH | 2010年 / 345卷 / 10期

关键词：

Pyrrolidine; Iminosugar; Carbamate; Reductive amination; Green chemistry; Protecting group free; MODELING CHEMICAL-REACTIVITY; REDUCTIVE AMINATION; PROTECTING-GROUP; GLYCOSIDASE INHIBITORS; ALPHA-GLUCOSIDASE; NATURAL OCCURRENCE; D-LYXOSE; DERIVATIVES; ALDEHYDES; KETONES;

D O I：

10.1016/j.carres.2010.03.016

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1360 / 1365

页数：6

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