Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Brønsted Acid Catalysis. Issue 12 (14th February 2017)

• Record Type: Journal Article
• Authors: Shen, Dan; Chen, Qiliang; Yan, Peipei; Zeng, Xiaofei; Zhong, Guofu
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 12(2017)
• Page Start: 3242
• Page End: 3246
• Publication Date: 2017-02-14
• Subjects: allylic compounds -- enantioselectivities -- iridium -- organocatalysis -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201609693
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The combination of a transition‐metal catalyst and organocatalyst was designed to achieve a highly enantioselective system for the allylic dearomatization reaction of naphthols with racemic secondary allylic alcohols. The desired β‐naphthalenones, bearing an all‐carbon quaternary center, were obtained in good yields with high chemo‐ and enantioselectivities. The cooperative catalytic system, involving a chiral iridium complex and phosphoric acid, provided measurable improvements in yields, and chemo‐ and enantioselectivities relative to single‐catalyst systems. Control experiments indicated that the chiral iridium complex functions as a key species in the control of the absolute configuration, thus enabling the formation of both β‐naphthalenone enantiomers by simply employing opposite enantiomeric ligands. Abstract : Co‐op : The cooperative dual‐catalytic system of a chiral iridium complex and phosphoric acid achieves highly enantioselective allylic dearomatization reactions of naphthols with racemic secondary allylic alcohols. The desired β‐naphthalenones, bearing an all‐carbon quaternary center, were obtained in good yields. Both β‐naphthalenone enantiomers can be obtained by simply employing opposite enantiomeric ligands.