Abstract
Stereoselective routes to N-Ph 2PO-protected cis and trans meso-aziridino cyclohexene oxides have been developed. Enantioselective rearrangement of the cis epoxide with chiral bases gave the allylic alcohol in a maximum of 47% ee whilst that of the trans epoxide proceeded with enantioselectivity of up to 68% ee. Both these results demonstrate for the first time that chiral bases which smoothly rearrange epoxides to allylic alcohols do not react with N-Ph 2PO-protected aziridines.
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