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Issue 10, 2016
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Catalytic asymmetric direct-type 1,4-addition reactions of simple esters

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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

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Supplementary files

Article information


Submitted
31 May 2016
Accepted
28 Jun 2016
First published
29 Jun 2016

Org. Chem. Front., 2016,3, 1241-1245
Article type
Research Article

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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