Tetraalkylammonium-templated stereoselective Norrish-Yang cyclization

Shinji Yamada; Azusa Iwaoka; Yuka Fujita; Seiji Tsuzuki

doi:10.1021/ol4028732

Tetraalkylammonium-templated stereoselective Norrish-Yang cyclization

Org Lett. 2013 Dec 6;15(23):5994-7. doi: 10.1021/ol4028732. Epub 2013 Nov 13.

Authors

Shinji Yamada¹, Azusa Iwaoka, Yuka Fujita, Seiji Tsuzuki

Affiliation

¹ 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.

PMID: 24224715
DOI: 10.1021/ol4028732

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzene Derivatives / chemistry*
Benzofurans / chemical synthesis*
Benzofurans / chemistry
Cations
Crystallography, X-Ray
Cyclization
Molecular Conformation
Molecular Structure
Quaternary Ammonium Compounds / chemistry*
Salts
Stereoisomerism

Substances

Benzene Derivatives
Benzofurans
Cations
Quaternary Ammonium Compounds
Salts