Abstract
Asymmetric synthesis of 2-alkyl-1-tetralones ( 2) was achieved in up to 91% e.e. by enantioselective protonation of their corresponding achiral lithium enolates ( 4) using a chiral amine (( R)- 1) as a chiral source in the presence of lithium bromide. Enantioselective alkylation using ( R)- 1 was also carried out, and it is found that the alkyl halide prefers the si-face of the lithium enolate 6 as oppose to the re-face preference of 4a in case of protonation.
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