The Journal of Organic Chemistry

Alkylation of allylic derivatives. 8. Regio-and stereochemistry of alkylation of allylic carboxylates with lithium methylcyanocuprate

HL Goering, SS Kantner

Index: Goering, Harlan L.; Kantner, Steven S. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 422 - 426

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Citation Number: 80

Abstract

Alkylation of 5-methyl-2-cyclohexenyl acetate (1-OAc) with lithium methylcyanocuprate (LiCu (CN) Me) is regiospecific (> W% excw y-alkylation) and stereospecific (> 95% anti alkylation). In the bicyclo [3.2. 1] oct&en-2-y1 system (3), alkylation is stereoselective (both isomers give exo alkylation) and regiospecific (excess y-alkylation). Alkylation of trans-a- methyl-y-mesitylallyl acetate (8-OAc) with LiCu (CN) Me gives 57% a-and 43% y- ...