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Synlett 1993; 1993(7): 513-514
DOI: 10.1055/s-1993-22512
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A Two-step Procedure for the Synthesis of Enantiomerically Pure N-Tosyl Homoallylic Amines

Malcolm B. Berry* , Donald Craig, Philip S. Jones
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, England
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Publication Date:
19 March 2002 (online)

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Sequential treatment of lithio(phenylsulfonyl)methane with enantiomerically pure N-tosylaziridines 2, n-butyllithium and aldehydes 3 gives ß-hydroxysulfones 5. Reductive elimination of crude 5 gives enantiomerically pure N-tosyl homoallylic amines 6 in high yield and with good to excellent E-selectivity.

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