Enantioselective Route to 5-Methyl- and 5,7-Dimethyl-6,7-dihydro-5H-dibenz[c,e]azepine: Secondary Amines with Switchable Axial Chirality

(−)-5-Methyl-6,7-dihydro-5H-dibenz[c,e]azepine 4, a new secondary amine featuring an axis-center stereochemical relay, was prepared enantioselectively from 2′-acetylbiphenyl-2-carboxylic acid, using (R)-2-phenylglycinol as an auxiliary for the control of both elements of chirality. The biaryl axis i...

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Bibliographic Details
Published in:Organic letters 2009-04, Vol.11 (7), p.1663-1666
Main Authors: Pira, Silvain L, Wallace, Timothy W, Graham, Jonathan P
Format: Article
Language:English
Subjects:
Amines - chemistry
Catalysis
Dibenzazepines - chemical synthesis
Dibenzazepines - chemistry
Molecular Structure
Stereoisomerism
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Summary:(−)-5-Methyl-6,7-dihydro-5H-dibenz[c,e]azepine 4, a new secondary amine featuring an axis-center stereochemical relay, was prepared enantioselectively from 2′-acetylbiphenyl-2-carboxylic acid, using (R)-2-phenylglycinol as an auxiliary for the control of both elements of chirality. The biaryl axis in 4 preferentially adopts the aS-configuration, with the methyl substituent pseudoequatorial, but conversion into the corresponding N-Boc derivative locks the axis into the aR-configuration, as predicted on the basis of molecular mechanics calculations.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900333c