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© Georg Thieme Verlag Stuttgart, New York Synlett 2015.Conjugate addition of enantiopure lithium (R)-N-benzyl-N-(α-methylbenzyl)amide to a range of ω-aryl-α,β-unsaturated esters gives the corresponding ω-aryl-β-amino esters as single diastereoisomers in high yields. Friedel-Crafts cyclisation of the pendant carbonyl group onto the ω-aryl ring then gives a range of 3-amino-substituted 1-indanones, 1-tetralones, and 1-benzosuberones, representing an efficient and short protocol for the preparation of these benzo-fused carbocycles in enantiopure form.

Original publication

DOI

10.1055/s-0034-1380675

Type

Journal article

Journal

Synlett

Publication Date

01/07/2015

Volume

26

Pages

1541 - 1544