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Letters in Organic Chemistry

Author(s): H. Zhang, W. H. Chan, Albert W.M. Lee, P.- F. Xia and W. Y. Wong

DOI: 10.2174/1570178043488644

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Asymmetric 1,3-Dipolar Cycloaddition of Chiral α, β-Unsaturated-γ-Sultams with Nitrile Oxides and Nitrones

Page: [63 - 66] Pages: 4

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Abstract

The scope and limitations of 1,3-dipolar cycloaddition reactions between nitrile oxides and chiral α,β-unsaturated-γ-sultams 2a and 2b have been investigated. Only very marginal diastereoselectivity was observed for the reaction. In contrast, using double asymmetric induction strategy, the cycloaddition products from 2a and chiral nitrones were obtained in better diastereomeric ratios (up to 7.1:1).

Keywords: dipolar, cycloaddition, chiral sultams, nitrile oxides, nitrones