[3+2] Cycloaddition on Carbohydrate Templates: Stereoselective Synthesis of Pyrrolidines

被引：21

作者：

Cai, Shuting ^{[1
]}

Gorityala, Bala Kishan ^{[1
]}

Ma, Jimei ^{[1
]}

Leow, Min Li ^{[1
]}

Liu, Xue-Wei ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 05期

关键词：

ETHER NAZAROV CYCLIZATION; ASYMMETRIC-SYNTHESIS; CHIRAL AUXILIARIES; DIASTEREOSELECTIVE SYNTHESIS; HETEROCYCLIC-COMPOUNDS; ACID; DERIVATIVES; INHIBITORS; CATALYST; ANALOGS;

D O I：

10.1021/ol103119u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyrrolidine derivatives were prepared in high diastereoselectivities and good yields via a [3 + 2] cycloaddition of a tert-butyldimethylsilyl protected carbohydrate-based allene with a diverse range of imines. The subsequent removal of the carbohydrate auxiliary afforded a variety of pyrrolidines with excellent enantioselectivities (up to 99% ee). Selective reduction of the pyrrolidines further demonstrated the potential of this strategy.

引用

页码：1072 / 1075

页数：4

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