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

Smriti Koodanjeri; V. Ramamurthy

doi:10.1016/S0040-4039(02)02231-1

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

Smriti Koodanjeri, V. Ramamurthy

Research output: Contribution to journal › Article › peer-review

32 Scopus citations

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 language	English (US)
Pages (from-to)	9229-9232
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4039(02)02231-1
State	Published - Dec 9 2002
Externally published	Yes

Keywords

Chiral induction
Cyclodextrin
Diphenylcyclopropane
Photoisomerization

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/S0040-4039(02)02231-1

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title = "Cyclodextrin mediated enantio and diastereoselective geometric photoisomerization of diphenylcyclopropane and its derivatives",

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.",

keywords = "Chiral induction, Cyclodextrin, Diphenylcyclopropane, Photoisomerization",

author = "Smriti Koodanjeri and V. Ramamurthy",

note = "Funding Information: The authors thank the National Science Foundation for support of the research (CHE-9904187 and CHE-0212042), Ajit Pradhan for help with solid state NMR and J. Sivaguru for help with the synthesis of the systems used in this study. ",

year = "2002",

month = dec,

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doi = "10.1016/S0040-4039(02)02231-1",

language = "English (US)",

volume = "43",

pages = "9229--9232",

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TY - JOUR

T1 - Cyclodextrin mediated enantio and diastereoselective geometric photoisomerization of diphenylcyclopropane and its derivatives

AU - Koodanjeri, Smriti

AU - Ramamurthy, V.

N1 - Funding Information: The authors thank the National Science Foundation for support of the research (CHE-9904187 and CHE-0212042), Ajit Pradhan for help with solid state NMR and J. Sivaguru for help with the synthesis of the systems used in this study.

PY - 2002/12/9

Y1 - 2002/12/9

N2 - 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.

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.

KW - Chiral induction

KW - Cyclodextrin

KW - Diphenylcyclopropane

KW - Photoisomerization

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U2 - 10.1016/S0040-4039(02)02231-1

DO - 10.1016/S0040-4039(02)02231-1

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 50

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