Catalytic asymmetric [2+2] cycloaddition between quinones and fulvenes and a subsequent stereoselective isomerization to 2, 3-dihydrobenzofurans. Issue 49 (5th June 2017)

• Record Type: Journal Article
• Authors: Zheng, Haifeng; Xu, Chaoran; Wang, Yan; Kang, Tengfei; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming
• Is Part Of: Chemical communications. Volume 53:Issue 49(2017)
• Page Start: 6585
• Page End: 6588
• Publication Date: 2017-06-05
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc03211k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A chiral Lewis acid catalyzed enantioselective [2+2] cycloaddition between quinones and fulvenes was reported for the first time. The method afforded a series of [6, 4, 5]-tricyclic cyclobutane derivatives in good yields with excellent regio- and stereoselectivities. Furthermore, the [2+2] adducts could be easily converted into formal [3+2] adducts efficiently and stereoselectively. Abstract : The catalytic enantioselective [2+2] cycloaddition between quinones and fulvenes was achieved, for the first time, by the use of a chiral copper(ii ) complex catalyst. The transformation afforded a series of enantiomerically enriched [6, 4, 5]-tricyclic cyclobutane derivatives in good yields with excellent regio- and stereoselectivities. Furthermore, the [2+2] adducts could be easily converted into formal [3+2] adducts efficiently and stereoselectively.