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Synlett 2015; 26(11): 1541-1544
DOI: 10.1055/s-0034-1380675
DOI: 10.1055/s-0034-1380675
letter
Enantiopure 3-Amino-Substituted 1-Indanones, 1-Tetralones, and 1-Benzosuberones via Friedel–Crafts Cyclisation of ω-Aryl-β-benzamido Acids
Weitere Informationen
Publikationsverlauf
Received: 06. März 2015
Accepted: 03. April 2015
Publikationsdatum:
20. Mai 2015 (online)


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.