Studies toward the photochemical synthesis of functionalized [5]- and [6]carbohelicenes

Morwenna S M Pearson; David R Carbery

doi:10.1021/jo900785k

Studies toward the photochemical synthesis of functionalized [5]- and [6]carbohelicenes

Morwenna S M Pearson, David R Carbery

Department of Chemistry

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

33 Citations (SciVal)

Abstract

An efficient route to nonsymmetrical helical menthyl esters by means of an oxidative photocyclization reaction of dissymmetric bis-stilbenes is reported. The developed route allows the introduction of functionality on rings A, E, or F, and the influence of the substituent pattern on the photochemical reaction has been examined. Diastereoselectivity is observed when a double chiral induction strategy with dimenthyl helicene esters synthesized in a 70:30 ratio of isomers is used.

Original language	English
Pages (from-to)	5320-5325
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	74
Issue number	15
DOIs	https://doi.org/10.1021/jo900785k
Publication status	Published - 2009

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10.1021/jo900785k

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title = "Studies toward the photochemical synthesis of functionalized [5]- and [6]carbohelicenes",

abstract = "An efficient route to nonsymmetrical helical menthyl esters by means of an oxidative photocyclization reaction of dissymmetric bis-stilbenes is reported. The developed route allows the introduction of functionality on rings A, E, or F, and the influence of the substituent pattern on the photochemical reaction has been examined. Diastereoselectivity is observed when a double chiral induction strategy with dimenthyl helicene esters synthesized in a 70:30 ratio of isomers is used.",

author = "Pearson, {Morwenna S M} and Carbery, {David R}",

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AU - Pearson, Morwenna S M

AU - Carbery, David R

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N2 - An efficient route to nonsymmetrical helical menthyl esters by means of an oxidative photocyclization reaction of dissymmetric bis-stilbenes is reported. The developed route allows the introduction of functionality on rings A, E, or F, and the influence of the substituent pattern on the photochemical reaction has been examined. Diastereoselectivity is observed when a double chiral induction strategy with dimenthyl helicene esters synthesized in a 70:30 ratio of isomers is used.

AB - An efficient route to nonsymmetrical helical menthyl esters by means of an oxidative photocyclization reaction of dissymmetric bis-stilbenes is reported. The developed route allows the introduction of functionality on rings A, E, or F, and the influence of the substituent pattern on the photochemical reaction has been examined. Diastereoselectivity is observed when a double chiral induction strategy with dimenthyl helicene esters synthesized in a 70:30 ratio of isomers is used.

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UR - http://dx.doi.org/10.1021/jo900785k

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JF - Journal of Organic Chemistry

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Studies toward the photochemical synthesis of functionalized [5]- and [6]carbohelicenes

Abstract

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AN EXPLORATION OF HELICAL ASYMMETRY - DEVELOPMENT AND APPLIC ATINO OF HELICAL ORGANOCATALYSTS

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Studies toward the photochemical synthesis of functionalized [5]- and [6]carbohelicenes

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AN EXPLORATION OF HELICAL ASYMMETRY - DEVELOPMENT AND APPLIC ATINO OF HELICAL ORGANOCATALYSTS

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