Issue 64, 2018

Dynamic kinetic asymmetric transformations of β-halo-α-keto esters by N,N′-dioxide/Ni(ii)-catalyzed carbonyl-ene reaction

Abstract

Dynamic kinetic asymmetric transformations of racemic β-halo-α-keto esters through carbonyl-ene reaction were realized using a chiral N,N′-dioxide-nickel(II) complex, giving the corresponding β-halo-α-hydroxy esters containing two vicinal chiral tri- and tetrasubstituted carbon centers in good yields and dr with excellent ee values without the use of extra bases. Meanwhile, a proposed reaction mechanism was presented according to the configuration of the product.

Graphical abstract: Dynamic kinetic asymmetric transformations of β-halo-α-keto esters by N,N′-dioxide/Ni(ii)-catalyzed carbonyl-ene reaction

Supplementary files

Article information

Article type
Communication
Submitted
22 Jun 2018
Accepted
16 Jul 2018
First published
17 Jul 2018

Chem. Commun., 2018,54, 8901-8904

Dynamic kinetic asymmetric transformations of β-halo-α-keto esters by N,N′-dioxide/Ni(II)-catalyzed carbonyl-ene reaction

W. Liu, W. Cao, H. Hu, L. Lin and X. Feng, Chem. Commun., 2018, 54, 8901 DOI: 10.1039/C8CC04993A

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