The benzhydryl group is the key: Efficient alkylation of 3-substituted aziridine-2-carboxylates is only possible with N-benzhydryl-protected aziridines and occurs with complete retention of the configuration at the 2-position. Sequential catalytic asymmetric aziridination and aziridine alkylation reactions have been applied to the synthesis of BIRT-377 (see structure).
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Patwardhan et al. (2005) studied this question.
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