Studies on Lewis Acid-Catalysed Generation and Intermolecular Trapping of Chiral Stabilised Azomethine Ylids

Laurence M. Harwood; Ajith C. Manage; Sylvie Robin; Simon F. G. Hopes; David J. Watkin; C. Eleri Williams

doi:10.1055/s-1993-22606

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Synlett 1993; 1993(10): 777-780
DOI: 10.1055/s-1993-22606

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Studies on Lewis Acid-Catalysed Generation and Intermolecular Trapping of Chiral Stabilised Azomethine Ylids

Laurence M. Harwood^* , Ajith C. Manage, Sylvie Robin, Simon F. G. Hopes, David J. Watkin, C. Eleri Williams

^*Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY, England

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Publication Date:
19 March 2002 (online)

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Preparation of the ylid (2) derived from 5(R)-phenylmorpholinone (1) in the presence of freshly prepared MgBr₂·Et₂O and dipolarophiles can lead to improved cycloaddition yields, with inverse diastereo- and regioselection compared to the corresponding uncatalysed reactions.

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