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

Reference:

Pearson, M. S. M. and Carbery, D. R., 2009. Studies toward the photochemical synthesis of functionalized [5]- and [6]carbohelicenes. Journal of Organic Chemistry, 74 (15), pp. 5320-5325.

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Official URL:

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

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.

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