Issue 42, 2016

Gold(i) catalyzed tandem cyclization of propargylic esters to 4-acyloxy-1,2-dihydroquinolines

Abstract

An effective synthetic protocol for structurally diverse 4-acyloxy-1,2-dihydroquinoline compounds has been accomplished by a gold(I)-catalyzed tandem [3,3]-rearrangement and intramolecular hydroamination of propargylic esters, affording the desired products in good yields. Moreover, the asymmetric variant of this cyclization has also been achieved using a chiral nitrogen acyclic carbene (NAC) gold(I) complex. These products have application in the enantioselective synthesis of an aromatase inhibitor within three simple steps.

Graphical abstract: Gold(i) catalyzed tandem cyclization of propargylic esters to 4-acyloxy-1,2-dihydroquinolines

Supplementary files

Article information

Article type
Communication
Submitted
14 Apr 2016
Accepted
26 Apr 2016
First published
27 Apr 2016

Chem. Commun., 2016,52, 6942-6945

Gold(I) catalyzed tandem cyclization of propargylic esters to 4-acyloxy-1,2-dihydroquinolines

Y. Sun, P. Gu, Y. Gao, Q. Xu and M. Shi, Chem. Commun., 2016, 52, 6942 DOI: 10.1039/C6CC03132C

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