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Engineering acyclic alkyl aryl ketones for enantioselective Norrish/Yang type II photochemistry in the crystalline state

TitleEngineering acyclic alkyl aryl ketones for enantioselective Norrish/Yang type II photochemistry in the crystalline state
Publication TypeJournal Article
Year of Publication2006
AuthorsXia, WJ, Yang, C, Scheffer, JR, Patrick, BO
JournalCrystengcomm
Volume8
Pagination388-390
Type of ArticleArticle
ISBN Number1466-8033
KeywordsASYMMETRIC INDUCTION, REACTIVITY, SOLID-STATE
Abstract

While most alkyl aryl ketones fail to undergo the Norrish/Yang type II photoreaction in the solid state because they crystallize in conformations unfavorable for gamma-hydrogen atom abstraction, it was found with the aid of molecular mechanics that such is not the case for the 2-ethyl-1-arylbutan-1-one system; subsequent application of the solid state ionic chiral auxiliary method of asymmetric synthesis to derivatives of this ketone afforded the corresponding Yang cyclobutanol in enantiomeric excesses as high as 92% at 91% conversion.

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