Chemistry of aldolate dianions. Effects of. beta.-heteroatom substituents on ketone enolization

VA Martin, DH Murray, NE Pratt, YB Zhao…

Index: Van Martin; Murray, Desmond H.; Pratt, Norman E.; Zhao, Yun-Bo; Albizati, Kim F. Journal of the American Chemical Society, 1990 , vol. 112, # 19 p. 6965 - 6978

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Citation Number: 46

Abstract

Abstract:@-Hydroxy ketones can be doubly deprotonated with> 2 equiv of an amide base at low temperature providing both proximal or distal aldolate dianions in good to excellent yield. A variety of substitutionally biased@-hydroxy ketones give exclusively distal dianions. If the distal site is blocked, proximal dianions are formed in good yield; however, chromatographic separation of the silylated products leads to decreased yields. ...

~79%

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