Organic letters

Direct synthesis of anti-1, 3-diols through nonclassical reaction of aryl Grignard reagents with isopropenyl acetate

Y Jiao, C Cao, Z Zhou

Index: Jiao, Yinchun; Cao, Chenzhong; Zhou, Zaichun Organic Letters, 2011 , vol. 13, # 2 p. 180 - 183

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Citation Number: 8

Abstract

A series of symmetrical aromatic 1, 3-diols were efficiently synthesized from substituted aryl Grignard reagents and isopropenyl acetate in a one-step reaction that formed anti products as the major species. Both experimental and theoretical studies suggested that the reaction involves the formation of a relatively stable intermediate E containing a six-membered ring from intermediate A. The stereoselectivity of the reactions and the molecular structure of ...