Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

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• 作者：Ryan W.F. Kerr^a ; Mark D. Greenhalgh^a ; Alexandra M.Z. Slawin^a ; Polly L. Arnold^b ; ^{polly.arnold@ed.ac.uk} ; Andrew D. Smith^a ; ^{ads10@st-andrews.ac.uk}
• 刊名：Tetrahedron: Asymmetry
• 出版年：2017
• 出版时间：15 January 2017
• 年：2017
• 卷：28
• 期：1
• 页码：125-134
• 全文大小：1612 K
• 卷排序：28

文摘

An enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations.