The Journal of Organic Chemistry

Stereochemistry of alkylation of carboxylic acid salt and ester. alpha. anions derived from cyclic systems

AP Krapcho, EA Dundulis

Index: Krapcho, A.Paul; Dundulis, Edward A. Journal of Organic Chemistry, 1980 , vol. 45, # 16 p. 3236 - 3245

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Citation Number: 46

Abstract

A stereochemical study of the alkylation of a-lithiated carboxylate salts and esters has been performed. The a anions derived from the bicyclic acids exo-1, endo-1, and 7 (R= H) and the esters 4 and 7 (R= CH3) yield predominantly exo alkylation. As an example, the a anion derived from ester 7 (R= CH,) on treatment with CHJ yields exo-8 (R= R'= CH3) and endo-9 (R= R= CHJ in a 97: 3 ratio, a highly stereoselective reaction. Addition of TMEDA to the ...