ChemInform Abstract: Activated Michael Acceptors as Precursors to Heterocycles. Part 1. 2‐Azetidinones from 2‐(Arylsulfonyl)propenoyl Chlorides and Amines.

Abstract

Activated Michael Acceptors as Precursors to Heterocycles. Part 1.2-Azetidinones from 2-(Arylsulfonyl)propenoyl Chlorides and Amines.-Azetidinones (II), (VII), and (IX) are formed as major or exclusive 1,4-addition products in the reaction of ammonia and primary amines with sulfonyl compounds (I). Fluorine as electron-withdrawing substituent in the arylsulfonyl group increases the ratio of azetidine to amide products. The addition of prochiral amine (VIII) to compound (Ia) gives a 68:32 mixture of diastereomers with main isomer (IX). Azetidinones (IIa), (IIc), and (VIIc) are examined in sulfonation and deprotection reactions. Phenylthio and phenylsulfoxo substituents as in compounds (X) and (XII) do not promote the formation of azetidinones. -(ZHOU, F.; ROSEN, J.; ZEBROWSKI-YOUNG, J. M.; FREIHAMMER, P. M.; DETTY, M. R.; LACHICOTTE, R.