Chiral N, N′‐Dioxide–Scandium(III)‐Catalyzed Asymmetric Dearomatization of 2‐Naphthols through an Amination Reaction. Issue 48 (9th October 2015)

• Record Type: Journal Article
• Authors: Lian, Xiangjin; Lin, Lili; Wang, Guojin; Liu, Xiaohua; Feng, Xiaoming
• Is Part Of: Chemistry. Volume 21:Issue 48(2015)
• Page Start: 17453
• Page End: 17458
• Publication Date: 2015-10-09
• Subjects: amination reaction -- asymmetric catalysis -- dearomatization -- naphthols -- scandium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201503276
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A catalytic asymmetric dearomatization of 2‐naphthols with azodicarboxylates has been accomplished by using a N, N′ ‐dioxide‐scandium(III) complex as a chiral catalyst. A number of optically active β‐naphthalenone compounds with a nitrogen‐containing quaternary carbon stereocenter were obtained in up to 99 % yield and up to 99 % ee under mild reaction conditions. The reaction could be scaled up to a gram‐scale with the yield and ee maintained. Based on these experiments and on previous reports, a possible transition state was proposed. Abstract : Animate you aminations ! A catalytic asymmetric dearomatization of 2‐naphthols with azodicarboxylates has been accomplished by using a N, N′ ‐dioxide–scandium(III) complex as a chiral catalyst (see scheme). A number of optically active β‐naphthalenone compounds with a nitrogen‐containing quaternary carbon stereocenter were obtained under mild reaction conditions.