The Journal of Organic Chemistry

. beta.-Hydroxy esters:(E)-versus (Z)-enolate geometry in dianionic Claisen rearrangements

MJ Kurth, RL Beard

Index: Kurth, Mark J.; Beard, Richard L. Journal of Organic Chemistry, 1988 ,  vol. 53,  # 17  p. 4085 - 4088

Full Text: HTML

Citation Number: 21

Abstract

In order to verify the l-CJC, stereochemical assignments of the@-hydroxy ester dianion Claisen products from 7 and 13, the corresponding uC,/C, P-hydroxy esters were prepared by aldol condensation. Thus, alcohol 6 was acetylated and the resulting acetate was employed in an Ireland enolate-Claisen rearrangement. Subsequent diazomethane esterification provided methyl ester 18, the lithium enolate of which was condensed with ...