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Asymmetric dipolar cycloaddition reactions: a practical, convergent synthesis of chiral pyrrolidines

โœ Scribed by Zhenkun Ma; Sanyi Wang; Curt S. Cooper; Anthony K.L. Fung; John K. Lynch; Frederick Plagge; Daniel T.W. Chu

Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
341 KB
Volume
8
Category
Article
ISSN
0957-4166

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โœฆ Synopsis

Chiral trans-3,4-disubstituted pyrrolidines were obtained from the 1,3-dipolar cycloaddition of chiral ot,/~-unsaturated N-acyloxazolidinones and azomethine ylide.

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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

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