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Asymmetric synthesis of 1,3- and 1,3,4-substituted pyrrolidines

โœ Scribed by Jing Lin; Wing Hong Chan; Albert W.M Lee; Wai Yeung Wong; Pei Qiang Huang

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
102 KB
Volume
41
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Diastereoselective alkylation of N-acylnorbornene sultams 2 afforded a variety of enantiomerically pure products 3a-3e. Reduction with LiAlH 4 (LAH) followed by ditosylation furnished chiral 1,4-ditosylates 5a-5e which underwent a cyclization reaction with primary amines to afford chiral 1,3-and 1,3,4-substituted pyrrolidines.

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Thiazolium ylids 2a and 2b are converted to 4 in 3 steps. Summary: The 1,3-dipolar cycloaddition of azomethine ylids with activated alkenes constitutes an effective synthetic method for certain pyrrolidines. 1 However, the reaction is rather limited in that R and R' are invariably aryl substituents