Tetrahedron: asymmetry

Synthesis of novel C 2-symmetric and enantiomerically pure bisbenzoxazoles and bisbenzothiazoles derived from l-and d-tartaric acids

P Jiao, J Xu, Q Zhang, MCK Choi, ASC Chan

Index: Jiao, Peng; Xu, Jiaxi; Zhang, Qihan; Choi, Michael C.K.; Chan, Albert S.C. Tetrahedron Asymmetry, 2001 , vol. 12, # 22 p. 3081 - 3088

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Citation Number: 18

Abstract

Five pairs of novel C2-symmetric and enantiomerically pure bisbenzoxazoles and a pair of bisbenzothiazoles derived from l-and d-tartaric acids have been synthesized from l-and d-2, 3-O-isopropylidenetartaric dichlorides and o-aminophenol derivatives or o-aminothiophenol, respectively, in two-or one-step reactions. The mechanism for the formation of bisbenzoxazoles and bisbenzothiazoles was suggested. The UV and 1H NMR spectra ...