Enantioselective route to 5-methyl-And 5,7-dimethyl-6,7-dihydro-sh- dibenz[c,e]azepine: Secondary amines with switchable axial chirality

Silvain L. Pira; Timothy W. Wallace; Jonathan P. Graham

doi:10.1021/ol900333c

Enantioselective route to 5-methyl-And 5,7-dimethyl-6,7-dihydro-sh- dibenz[c,e]azepine: Secondary amines with switchable axial chirality

Silvain L. Pira, Timothy W. Wallace, Jonathan P. Graham

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Abstract

(-) -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. © 2009 American Chemical Society.

Original language	English
Pages (from-to)	1663-1666
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	7
DOIs	https://doi.org/10.1021/ol900333c
Publication status	Published - 2 Apr 2009

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CCDC 712972: Experimental Crystal Structure Determination
Pira, S. L. (Contributor), Wallace, T. (Contributor) & Graham, J. P. (Contributor), Cambridge Crystallographic Data Centre, 2008
DOI: 10.5517/ccrxx3n, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccrxx3n&sid=DataCite
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@article{cf030da8ed5e4facaf12e7e2e809ab9b,

title = "Enantioselective route to 5-methyl-And 5,7-dimethyl-6,7-dihydro-sh- dibenz[c,e]azepine: Secondary amines with switchable axial chirality",

abstract = "(-) -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. {\textcopyright} 2009 American Chemical Society.",

author = "Pira, {Silvain L.} and Wallace, {Timothy W.} and Graham, {Jonathan P.}",

year = "2009",

month = apr,

day = "2",

doi = "10.1021/ol900333c",

language = "English",

volume = "11",

pages = "1663--1666",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

T1 - Enantioselective route to 5-methyl-And 5,7-dimethyl-6,7-dihydro-sh- dibenz[c,e]azepine: Secondary amines with switchable axial chirality

AU - Pira, Silvain L.

AU - Wallace, Timothy W.

AU - Graham, Jonathan P.

PY - 2009/4/2

Y1 - 2009/4/2

N2 - (-) -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. © 2009 American Chemical Society.

AB - (-) -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. © 2009 American Chemical Society.

U2 - 10.1021/ol900333c

DO - 10.1021/ol900333c

M3 - Article

SN - 1523-7052

VL - 11

SP - 1663

EP - 1666

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Enantioselective route to 5-methyl-And 5,7-dimethyl-6,7-dihydro-sh- dibenz[c,e]azepine: Secondary amines with switchable axial chirality

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CCDC 712972: Experimental Crystal Structure Determination

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