Reactive-state spin-dependent diastereoselective photoisomerization of trans,trans-2,3-diphenylcyclopropane-1-carboxylic acid derivatives included in zeolites

J. Sivaguru; Tetsuya Shichi; V. Ramamurthy

doi:10.1021/ol026695l

Reactive-state spin-dependent diastereoselective photoisomerization of trans,trans-2,3-diphenylcyclopropane-1-carboxylic acid derivatives included in zeolites

J. Sivaguru, Tetsuya Shichi, V. Ramamurthy

Research output: Contribution to journal › Article

23 Scopus citations

Abstract

(equation presented) The asymmetric induction facilitated by a chiral auxiliary during the photoisomerization of trans,trans-2,3-diphenylcyclopropane derivatives depends on the medium (solution vs zeolite) and the reactive state (singlet vs triplet). Within zeolites, direct excitation most likely proceeds via a zwitterionic intermediate, while triplet sensitization most likely proceeds via a diradical intermediate.

Original language	English (US)
Pages (from-to)	4221-4224
Number of pages	4
Journal	Organic letters
Volume	4
Issue number	24
DOIs	https://doi.org/10.1021/ol026695l
State	Published - Nov 28 2002
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol026695l

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Sivaguru, J., Shichi, T., & Ramamurthy, V. (2002). Reactive-state spin-dependent diastereoselective photoisomerization of trans,trans-2,3-diphenylcyclopropane-1-carboxylic acid derivatives included in zeolites. Organic letters, 4(24), 4221-4224. https://doi.org/10.1021/ol026695l

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abstract = "(equation presented) The asymmetric induction facilitated by a chiral auxiliary during the photoisomerization of trans,trans-2,3-diphenylcyclopropane derivatives depends on the medium (solution vs zeolite) and the reactive state (singlet vs triplet). Within zeolites, direct excitation most likely proceeds via a zwitterionic intermediate, while triplet sensitization most likely proceeds via a diradical intermediate.",

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AB - (equation presented) The asymmetric induction facilitated by a chiral auxiliary during the photoisomerization of trans,trans-2,3-diphenylcyclopropane derivatives depends on the medium (solution vs zeolite) and the reactive state (singlet vs triplet). Within zeolites, direct excitation most likely proceeds via a zwitterionic intermediate, while triplet sensitization most likely proceeds via a diradical intermediate.

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