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Enantioselective [4+2] Cycloaddition of Cyclic N-Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones

ORGANIC LETTERS (2013)

期刊

ORGANIC LETTERS

卷 15, 期 23, 页码 6090-6093

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol402977w

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Chemistry, Organic

资金

NSFC [21102116]
Science & Technology Department of Sichuan Province [2013JY0095]

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Reagent

摘要

A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported.

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