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Molecules 2017, 22(5), 784; doi:10.3390/molecules22050784

Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, China
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Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 6 February 2017 / Revised: 8 May 2017 / Accepted: 9 May 2017 / Published: 12 May 2017
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

The ortho-nitro effect was discovered in sulfa-Staudinger cycloadditions of ethoxycarbonylsulfene with linear imines. When an ortho-nitro group is present at the C-aryl substituents of linear imines, the sulfa-Staudinger cycloadditions deliver cis-β-sultams in considerable amounts, together with the predominant trans-β-sultams. In other cases, the above sulfa-Staudinger cycloadditions give rise to trans-β-sultams exclusively. Further mechanistic rationalization discloses that the ortho-nitro effect is attributed to its strong electron-withdrawing inductive effect. Similarly, the ortho-nitro effect also exists in Staudinger cycloadditions of ethoxycarbonyl ketene with the imines. The current research provides further insights into the diastereoselective control in sulfa-Staudinger and Staudinger cycloadditions. View Full-Text
Keywords: nitro effect; diastereoselectivity; inductive effect; sulfa-Staudinger cycloaddition; Staudinger cycloaddition; stereochemistry nitro effect; diastereoselectivity; inductive effect; sulfa-Staudinger cycloaddition; Staudinger cycloaddition; stereochemistry
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MDPI and ACS Style

Yang, Z.; Abdellaoui, H.; He, W.; Xu, J. Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions. Molecules 2017, 22, 784.

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