Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes

H Sugihara, K Daikai, XL Jin, H Furuno, J Inanaga

Index: Sugihara, Hiroyasu; Daikai, Kazuhiro; Jin, Xiu Lan; Furuno, Hiroshi; Inanaga, Junji Tetrahedron Letters, 2002 , vol. 43, # 15 p. 2735 - 2739

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Citation Number: 39

Abstract

Optically active N-unsubstituted α-keto aziridines 2 were synthesized from conjugated enones 1 via the Sc [(R)-BNP] 3-catalyzed enantioselective Michael addition of O- methylhydroxylamine followed by the La (Oi-Pr) 3-catalyzed ring closure of the corresponding β-methoxyamino ketones 3. A remarkably high asymmetric amplification was observed during the Michael addition, and notable kinetic resolution was also realized ...