Studies toward the Photochemical Synthesis of Functionalized [5]- and [6]Carbohelicenes
- 25 June 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 74 (15) , 5320-5325
- https://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.Keywords
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