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

Author:
Sun, Yuan-Ming, Gu, Peng, Gao, Yu-Ning, Xu, Qin, Shi, Min
Source:
Chemical communications 2016 v.52 no.42 pp. 6942-6945
ISSN:
1364-548X
Subject:
aromatase, carbenes, cyclization reactions, enantioselective synthesis, enzyme inhibitors, esters, gold, nitrogen, unspecific monooxygenase
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.
Agid:
6387849