Journal of the American Chemical Society p. 4931 - 4936 (1991)
Update date:2022-08-03
Topics:
Schultz, Arthur G.
Green, Neal J.
Ortho-lithiation-alkylation of tertiary benzamide 3 provides a series of 2-substituted chiral benzatnides 3a-g (Scheme I). Birch reduction of 3a-j followed by alkylation of the resulting chiral amide enolate with Mel at -78 °C gives 1,6-di-alkyl-1,4-cyclohexadiene derivatives 4a-j with excellent diastereoselectivities (Table I). Applications of this asymmetric synthesis are illustrated by conversions of 4g to enantiomerically pure bicyclic lactone 9 and octalone 11 (Scheme III) and 4j to hexahydro-9-anthracenone 14 (Scheme IV).
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