Unusual reactivity of cis-2-benzoyl-1-benzyl-3-phenylaziridine with P-nucleophiles—ring opening vs. the Abramov reaction

Abstract

Thermal (80 °C) addition of dimethyl phosphite to cis-2-benzoyl-1-benzyl-3-phenylaziridine occurred exclusively at C(3) with concomitant cleavage of the C(2)–C(3) bond. The carbonyl group in the aminoketone produced under these conditions was reduced with hydrogen over Pearlman’s catalyst with low (20%) diastereoselectivity, while good (80%) de was observed in the NaBH₄ reduction as a result of the 1,4-asymmetric induction. The products of the Abramov reaction of the title compound were obtained (de 92%) when CsF was used as catalyst.