A new synthesis of pyrrolidines via imino-aldol reaction of (2-trimethylsilylmethyl) cyclopropyl ketones with imines

Yadav, Veejendra K. ; Gupta, Archana (2009) A new synthesis of pyrrolidines via imino-aldol reaction of (2-trimethylsilylmethyl) cyclopropyl ketones with imines Tetrahedron Letters, 49 (20). pp. 3212-3215. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2008.03.117

Abstract

A new synthesis of 2,3,5-trisubstituted pyrrolidines from the imino-aldols formed from Lewis acid-mediated reactions of (2-trimethylsilylmethyl)cyclopropyl ketones with benzylimines is described. The ring closure of the imino-aldols formed from the benzylimines of 2-chloro-, 2-fluoro-, and 2-trifluoromethylbenzaldehydes proceeds with predominantly 2,5-anti selectivity to generate the corresponding pyrrolidines in moderate yields.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:(2-Trimethylsilylmethyl)cyclopropyl Ketone; Enolate; Imino-aldol; Hg(II)-promoted Aza-ring Closure; 2,3,5-Trisubstituted Pyrrolidine
ID Code:58246
Deposited On:31 Aug 2011 06:57
Last Modified:31 Aug 2011 06:57

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