Journal
ORGANIC LETTERS
Volume 11, Issue 7, Pages 1663-1666Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900333c
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- EPSRC
- GlaxoSmithKline
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(-)-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.
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