Asymmetric synthesis using chiral acetals: Highly diastereoselective nucleophilic addition of Grignard reagents to chiral 1-oxo-.BETA.-tetralone 1-acetals.

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Abstract
Nucleophilic addition of organometallic reagents (Grignard reagents and organolithium reagents) to two chiral 1-oxo-β-tetralone 1-acetals (1a, b) was studied. Extremely high stereoselectivity was achieved in the reactions of 1a and 1b with Grignard reagents leading to the α-hydroxy acetals (6) bearing a chiral tertiary alcohol moiety at the homobenzylic position. The stereochemistry of the products derived from 1a was determined by correlation with compound 9 and that of the products derived from 1b was determined by consideration of the citcular dichroism spectrum of the benzoate (11) prepared from 6bC.

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