Highly efficient access to bi- and tricyclic ketals through gold-catalyzed tandem reactions of 4-acyl-1,6-diynes.
Single step: Fused bicyclic and bridged tricyclic ketals were synthesized in a single step from the reactions of easily available 4-acyl-1,6-diynes with H(2)O and alkanols (see scheme). The highly efficient AuCl(3)-catalyzed multicomponent domino reactions, involving five C-O bond formations, can proceed in a highly regio- and diastereoselective manner at room temperature under air and lead to structures of high molecular complexity from simple starting materials in an atom economic way.
Meng
Jia
J
Department of Chemistry, Northeast Normal University, Changchun, 130024, PR China.
Zhao
Yu-Long
YL
Ren
Chuan-Qing
CQ
Li
You
Y
Li
Zhu
Z
Liu
Qun
Q
D002384:Catalysis; D003500:Cyclization; D053280:Diynes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D053280:Diynes; D005663:Furans; D007659:Ketones; D006046:Gold