Abstract
Abstract Here, we report an empirical model for diastereoselective cyclopropanation of fumarate/maleate diesters with chloroacetate, sulfonium ylide, or ammonium ylide. With symmetrical fumarate/maleate diesters, cyclopropanation was found to proceed with a high level of diastereoselectivity in favor of the chiral isomer. In contrast, production of the meso isomer was observed in 38–48% diastereoselectivity when unsymmetrical fumarate/maleate was employed. An improved synthesis of (N-desmethy)dysibetaine CPa in both racemic and enantiomerically pure forms was furthermore achieved. Configurational analysis by experimental and calculated 13C NMR data is also reported.
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