Cyclodextrin mediated enantio and diastereoselective geometric photoisomerization of diphenylcyclopropane and its derivatives

Smriti Koodanjeri, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

cis-Diphenylcyclopropanes upon direct excitation and triplet sensitization undergo geometric isomerization to the corresponding trans isomers. In solution the trans isomers are formed as a 1:1 enantiomeric or diasteromeric mixture. Upon inclusion within β-cyclodextrin the same molecules give the trans isomers enriched in one optical isomer. Enantiomeric excess and diasteromeric excess induced by the optically active host β-cyclodextrin although small is mechanistically significant.

Original languageEnglish
Pages (from-to)9229-9232
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number50
DOIs
StatePublished - Dec 9 2002
Externally publishedYes

Fingerprint

Photoisomerization
Cyclodextrins
Isomers
Derivatives
Isomerization
Molecules
diphenylcyclopropane

Keywords

  • Chiral induction
  • Cyclodextrin
  • Diphenylcyclopropane
  • Photoisomerization

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Cyclodextrin mediated enantio and diastereoselective geometric photoisomerization of diphenylcyclopropane and its derivatives. / Koodanjeri, Smriti; Ramamurthy, Vaidhyanathan.

In: Tetrahedron Letters, Vol. 43, No. 50, 09.12.2002, p. 9229-9232.

Research output: Contribution to journalArticle

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AB - cis-Diphenylcyclopropanes upon direct excitation and triplet sensitization undergo geometric isomerization to the corresponding trans isomers. In solution the trans isomers are formed as a 1:1 enantiomeric or diasteromeric mixture. Upon inclusion within β-cyclodextrin the same molecules give the trans isomers enriched in one optical isomer. Enantiomeric excess and diasteromeric excess induced by the optically active host β-cyclodextrin although small is mechanistically significant.

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