Catalytic enantioselective alkylation of 2-alkoxy-tetrahydrofurans. Issue 16 (13th July 2020)

• Record Type: Journal Article
• Authors: Liu, Xuan; Sun, Shaofa; Wang, Gang; Bai, Zhushuang; Pang, Jingxiang; Liu, Lei
• Is Part Of: Organic chemistry frontiers. Volume 7:Issue 16(2020)
• Page Start: 2202
• Page End: 2206
• Publication Date: 2020-07-13
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo00104j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A nickel(ii )-catalyzed asymmetric alkylation of non-resonance-stabilized oxocarbenium ions with carboxylic acid derivatives on a large scale has been disclosed. Abstract : Catalytic asymmetric addition to non-resonance-stabilized oxocarbenium ions has remained a formidable challenge. Herein, we disclosed a nickel(ii )-catalyzed asymmetric alkylation of non-resonance-stabilized, five-membered oxocarbenium ions generated in situ from 2-alkoxy tetrahydrofurans with a broad range of carboxylic acid derivatives. The reaction exhibits high efficiency, excellent enantioselectivity, and good functional group tolerance, and can be conducted on a large scale. Aside from five-membered oxocarbenium ions, six-membered and acyclic aliphatic species were also well tolerated with excellent enantiocontrol, thus providing a practical and robust method to access enantiopure α-alkyl substituted saturated ethers.