Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates. Part 1: Formation of cis-aziridines |
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Authors: | JB Sweeney Alex A Cantrill Smita Thobhani |
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Institution: | a School of Chemistry, University of Bristol, Bristol BS8 1TS, UK b School of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, UK |
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Abstract: | The aza-Darzens (‘ADZ’) reactions of N-diphenylphosphinyl (‘N-Dpp’) imines with chiral enolates derived from oxazolidinones and camphorsultam have been studied. Whilst oxazolidinone enolates reacted poorly in terms of aziridination, the use of the chiral enolate derived from both antipodes of N-bromoacetyl 2,10-camphorsultam, 2R-(5) and 2S-(5), with N-diphenylphosphinyl aryl and tert-butylimines proceeded in generally good yield to give, respectively, (2′R,3′R)- or (2′S,3′S)-cis-N-diphenylphosphinyl aziridinoyl sultams of high de. |
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Keywords: | Aza-Darzens Aziridination Imine Camphorsultam |
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