Issue 17, 2017

Brønsted acid-catalyzed, enantioselective synthesis of 1,4-dihydroquinoline-3-carboxylates via in situ generated ortho-quinone methide imines

Abstract

A straightforward, catalytic, enantioselective approach toward the synthesis of a broad range of 1,4-dihydroquinoline-3-carboxylates is described. Under phosphoric acid catalysis in situ-generated ortho-quinone methide imines reacted with β-keto esters to form the nitrogen heterocycles with good yields and enantioselectivities in just one synthetic step under ambient reactions conditions.

Graphical abstract: Brønsted acid-catalyzed, enantioselective synthesis of 1,4-dihydroquinoline-3-carboxylates via in situ generated ortho-quinone methide imines

Supplementary files

Article information

Article type
Paper
Submitted
27 Feb 2017
Accepted
07 Apr 2017
First published
07 Apr 2017

Org. Biomol. Chem., 2017,15, 3706-3716

Brønsted acid-catalyzed, enantioselective synthesis of 1,4-dihydroquinoline-3-carboxylates via in situ generated ortho-quinone methide imines

T. Hodík and C. Schneider, Org. Biomol. Chem., 2017, 15, 3706 DOI: 10.1039/C7OB00488E

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