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Issue 16, 2020
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Catalytic enantioselective alkylation of 2-alkoxy-tetrahydrofurans

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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.

Graphical abstract: Catalytic enantioselective alkylation of 2-alkoxy-tetrahydrofurans

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Supplementary files

Article information


Submitted
21 Jan 2020
Accepted
29 Jun 2020
First published
13 Jul 2020

Org. Chem. Front., 2020,7, 2202-2206
Article type
Research Article

Catalytic enantioselective alkylation of 2-alkoxy-tetrahydrofurans

X. Liu, S. Sun, G. Wang, Z. Bai, J. Pang and L. Liu, Org. Chem. Front., 2020, 7, 2202
DOI: 10.1039/D0QO00104J

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