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Issue 11, 2020
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Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate

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Abstract

An enantioselective intermolecular carbonyl–ene reaction and a Friedel–Crafts-type reaction of 1,1,2-trisubstituted and 1,2-disubstituted simple olefins with ethyl glyoxylate were developed using F10BINOL-derived N-sulfonyl phosphoramide as the chiral strong Brønsted acid catalyst. The present reactions feature an atom-economical and environmentally benign approach to the synthesis of enantioenriched allylic and homoallylic alcohols.

Graphical abstract: Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate

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Supplementary files

Article information


Submitted
15 Apr 2020
Accepted
26 Apr 2020
First published
28 Apr 2020

Org. Chem. Front., 2020,7, 1383-1387
Article type
Research Article

Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate

J. Kikuchi, Y. Aizawa and M. Terada, Org. Chem. Front., 2020, 7, 1383
DOI: 10.1039/D0QO00448K

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