Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives. Issue 9 (7th August 2017)

• Record Type: Journal Article
• Authors: Zhang, Yu; Liao, Yuting; Liu, Xiaohua; Xu, Xi; Lin, Lili; Feng, Xiaoming
• Is Part Of: Chemical science. Volume 8:Issue 9(2017)
• Page Start: 6645
• Page End: 6649
• Publication Date: 2017-08-07
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc02809a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A highly enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using an N, N ′-dioxide–scandium(iii ) complex catalyst. This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Abstract : An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N, N ′-dioxide–scandium(iii ) complex catalyst. Various substituted ortho -quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed.