Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates. Part 2: Inversion of diastereoselectivity |
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Authors: | JB Sweeney Alex A Cantrill Andrew B McLaren |
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Institution: | a School of Chemistry, University of Reading, Reading RG1 5JN, UK b School of Chemistry, University of Bristol, Bristol BS8 1TS, UK |
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Abstract: | The aza-Darzens (‘ADZ’) reactions of N-diphenylphosphinyl (‘N-Dpp’) imines with chiral enolates derived from N-bromoacetyl 2S-2,10-camphorsultam proceed in generally good yield to give N-diphenylphosphinyl aziridinoyl sultams. However, the stereoselectivity of the reaction is dependent upon the structure of the imine substituent: when the chiral enolate was reacted with arylimines substituted in the ortho-position, mixtures of cis- and trans-2′R,3′R-aziridines were obtained, often with a complete selectivity in favour of the trans-isomer. |
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Keywords: | Aziridine Sultam Aza-Darzens |
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