Synlett 2015; 26(11): 1541-1544
DOI: 10.1055/s-0034-1380675
letter
© Georg Thieme Verlag Stuttgart · New York

Enantiopure 3-Amino-Substituted 1-Indanones, 1-Tetralones, and 1-Benzosuberones via Friedel–Crafts Cyclisation of ω-Aryl-β-benz­amido Acids

Stephen G. Davies*, Euan C. Goddard, Paul M. Roberts, Angela J. Russell, James E. Thomson
  • Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK   Email: steve.davies@chem.ox.ac.uk
Further Information

Publication History

Received: 06 March 2015

Accepted: 03 April 2015

Publication Date:
20 May 2015 (eFirst)

Dedicated to Peter Vollhardt on the occasion of his 69th birthday

Abstract

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.