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*
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK   eMail: steve.davies@chem.ox.ac.uk
,
Euan C. Goddard
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK   eMail: steve.davies@chem.ox.ac.uk
,
Paul M. Roberts
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK   eMail: steve.davies@chem.ox.ac.uk
,
Angela J. Russell
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK   eMail: steve.davies@chem.ox.ac.uk
,
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
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Publikationsverlauf

Received: 06. März 2015

Accepted: 03. April 2015

Publikationsdatum:
20. Mai 2015 (online)


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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.

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