Preparation of enantiomerically pure (1S,2S)-1-aminocyclopropanephosphonic acid from methylcyclopropanone acetal via spirophosphonate intermediates |
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| Institution: | 1. ENSCM – AM2N, UMR 5253 – Institut Charles Gerhardt, Montpellier Cedex 5, France;2. BCI Pharma, Cap Alpha, Clapiers, France;3. INSERM, Paris Cedex 13, France;4. Laboratoire de Chimie BioOrganique et de Substances Naturelles (LCBOSN), Université Nangui Abrogoua, Abidjan, Ivory Coast |
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| Abstract: | An easy and efficient one-pot reaction from readily available methylcyclopropanone acetal (2S)-4b gave the spirophosphonates 8a–b with excellent diastereoselectivity. These phosphonates, after catalytic hydrogenolysis and hydrolysis, furnished the enantiomerically pure (1S,2S)-1-amino-2-methylcyclopropanephosphonic acid 3b (analogue of (1R,2S)-allo-norcoronamic acid). |
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