Novel Intramolecular Induction of Axial Chirality by a Centrally Chiral Element in the Biphenyl Series

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Title:Novel Intramolecular Induction of Axial Chirality by a Centrally Chiral Element in the Biphenyl Series
Creators:
Tichý, Miloš
Günterová, Jana
Závada, Jiří
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 7, pp. 1080-1088
Uncontrolled Keywords:Induction of axial chirality, Bridged biphenyls

Abstract

The title induction has been observed in the reaction of achiral 2,2',6,6'-tetrakis(bromomethyl)biphenyl with centrally chiral (<i>R</i>)-1-phenylethylamine, (<i>R</i>)-1-(1-naphthyl)ethylamine and (<i>R</i>)-1-(2-naphthyl)ethylamine. The ratio of the arising diastereomeric doubly bridged diamines and their thermodynamic stability have been determined. The diastereomer excess in the kinetically controlled reaction is solvent-dependent. The absolute configuration of the biphenyl twist in the products has been assigned on the basis of CD spectra and comparison with singly bridged biphenyl models of known sense of the twist.

Title:Novel Intramolecular Induction of Axial Chirality by a Centrally Chiral Element in the Biphenyl Series
Creators:
Tichý, Miloš
Günterová, Jana
Závada, Jiří
Uncontrolled Keywords:Induction of axial chirality, Bridged biphenyls
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:7
Page Range:pp. 1080-1088
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19971080UNSPECIFIED
ID Code:1187
Item Type:Article
Deposited On:06 Feb 2009 17:07
Last Modified:06 Feb 2009 16:07

Citation

Tichý, Miloš; Günterová, Jana; Závada, Jiří (1997) Novel Intramolecular Induction of Axial Chirality by a Centrally Chiral Element in the Biphenyl Series. Collection of Czechoslovak Chemical Communications, 62 (7). pp. 1080-1088. ISSN 0010-0765

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