Issue 10, 2016

Catalytic asymmetric direct-type 1,4-addition reactions of simple esters

Abstract

In the presence of catalytic amounts of potassium hexamethyldisilazide (KHMDS) and a chiral macrocyclic crown ether, asymmetric 1,4-addition reactions of simple esters with α,β-unsaturated amides proceeded to afford the desired 1,4-adducts in high yields with good stereoselectivities. Mechanistic investigations revealed that proper combination of substrates was a key for the efficient catalytic turnover.

Graphical abstract: Catalytic asymmetric direct-type 1,4-addition reactions of simple esters

Supplementary files

Article information

Article type
Research Article
Submitted
31 Cam 2016
Accepted
28 Wax 2016
First published
29 Wax 2016

Org. Chem. Front., 2016,3, 1241-1245

Catalytic asymmetric direct-type 1,4-addition reactions of simple esters

I. Sato, H. Suzuki, Y. Yamashita and S. Kobayashi, Org. Chem. Front., 2016, 3, 1241 DOI: 10.1039/C6QO00242K

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