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Tetraalkylammonium-templated stereoselective Norrish-Yang cyclization
Shinji Yamada1, Azusa Iwaoka, Yuka Fujita
1Department of Chemistry, Ochanomizu University , Bunkyo-ku, Tokyo 112-8610, Japan, and National Institute of Advanced Industrial Science and Technology (AIST) , Tsukuba, Ibaraki 305-8568, Japan.
Abstract:
Tetrabutylammonium salts serve as templates for the Norrish-Yang cyclization of 2-benzyloxy-acylbenzenes to give trans-dihydrobenzofuranols in high stereoselectivities. The dual cation-π interactions between an ammonium with a benzene ring and a carbonyl group play a key role in changing the conformation of the substrate, which was supported by ab initio calculations.
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