Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids

Jonathan Clayden; Lluís Vallverdú; James Clayton; Madeleine Helliwell

doi:10.1039/b716105k

Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids

Jonathan Clayden^*, Lluís Vallverdú, James Clayton, Madeleine Helliwell

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

2 Citations (Scopus)

Abstract

Tertiary diamides of xanthene-1,8-dicarboxylic acid and biphenyl-2,2′-dicarboxylic acid exhibit a thermodynamic preference for anti stereochemistry which is inverted in the presence of Ti- or Sn-based Lewis acids, allowing interconversion between kinetically stable syn and anti diastereoisomeric atropisomers.

Original language	English
Pages (from-to)	561-563
Number of pages	3
Journal	Chemical Communications
Volume	8
Issue number	5
Early online date	28 Nov 2007
DOIs	https://doi.org/10.1039/b716105k
Publication status	Published - 7 Feb 2008

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title = "Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids",

abstract = "Tertiary diamides of xanthene-1,8-dicarboxylic acid and biphenyl-2,2′-dicarboxylic acid exhibit a thermodynamic preference for anti stereochemistry which is inverted in the presence of Ti- or Sn-based Lewis acids, allowing interconversion between kinetically stable syn and anti diastereoisomeric atropisomers.",

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T1 - Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids

AU - Clayden, Jonathan

AU - Vallverdú, Lluís

AU - Clayton, James

AU - Helliwell, Madeleine

PY - 2008/2/7

Y1 - 2008/2/7

N2 - Tertiary diamides of xanthene-1,8-dicarboxylic acid and biphenyl-2,2′-dicarboxylic acid exhibit a thermodynamic preference for anti stereochemistry which is inverted in the presence of Ti- or Sn-based Lewis acids, allowing interconversion between kinetically stable syn and anti diastereoisomeric atropisomers.

AB - Tertiary diamides of xanthene-1,8-dicarboxylic acid and biphenyl-2,2′-dicarboxylic acid exhibit a thermodynamic preference for anti stereochemistry which is inverted in the presence of Ti- or Sn-based Lewis acids, allowing interconversion between kinetically stable syn and anti diastereoisomeric atropisomers.

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DO - 10.1039/b716105k

M3 - Article (Academic Journal)

C2 - 18209789

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SN - 1359-7345

VL - 8

SP - 561

EP - 563

JO - Chemical Communications

JF - Chemical Communications

IS - 5

ER -

Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids

Abstract

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