Tetraalkylammonium-templated stereoselective Norrish-Yang cyclization.
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.
Department 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.
Shinji
S
Yamada
Azusa
A
Iwaoka
Yuka
Y
Fujita
Seiji
S
Tsuzuki
D001555:Benzene Derivatives / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002412:Cations; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012492:Salts; D013237:Stereoisomerism
D001555:Benzene Derivatives; D001572:Benzofurans; D002412:Cations; D000644:Quaternary Ammonium Compounds; D012492:Salts