Ring Opening of Pymisyl??Protected Aziridines with Organocuprates

J Bornholdt, J Felding, RP Clausen…

Index: Bornholdt, Jan; Felding, Jakob; Clausen, Rasmus P.; Kristensen, Jesper L. Chemistry - A European Journal, 2010 , vol. 16, # 41 p. 12474 - 12480

Full Text: HTML

Citation Number: 18

Abstract

Abstract The pyrimidine-2-sulfonyl (pymisyl) group is introduced as a new protecting group that can be used to activate aziridines towards ring opening. It is readily introduced and removed under mild conditions. Regioselective ring opening of pymisyl-protected 2-methyl- aziridine with organocuprates gives the corresponding sulfonamides in high yields, and the pymisyl group can subsequently be removed upon treatment with a thiolate. The versatility ...