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
收藏
页码：1360 / 1365
页数：6
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