Enantioselective synthesis of aziridine 2,2-dicarboxylates. Part 1: Copper(II)-bisoxazoline complex-catalysed Michael reaction on alkylidene malonates

摘要

The preparation of aziridine-2,2-dicarboxylates via 1,4-addition of N,O-bis(trimethylsilyl)hydroxylamine to alpha,beta-unsaturated malonates in the presence of chiral Lewis acids is reported. Good enantioselectivity was observed for conjugate addition catalysed by [Cu(S,S)-Bn-(box)](OTf)(2) on isobutylidene and 3-methylbutylidene malonate. (C) 2002 Elsevier Science Ltd. All rights reserved. [References: 23]