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Abstract

A synthetic method to prepare cycloalkyl‐ and (hetero)aryl‐fused bicyclo[3.3.1]nonane derivatives from gold(I)‐catalyzed cyclopropanation/[5+3] cycloaddition of 1,4,9‐ and 1,4,10‐allenenynes is described. The suggested double cycloisomerization mechanism delineates the first example of a stepwise [5+3] cycloaddition pathway in gold catalysis, a mode of reactivity that is also sparse in organic chemistry. Experimental and Density Functional Theory (DFT) computational studies based on a proposed gold carbenoid species provides insight into this unique selectivity that leads to the assembly of the architecturally challenging bridged carbocyclic motif.

Item Type:	Article
Authors/Creators:	Chen, X and Zhou, Y and Jin, J and Farshadfar, K and Ariafard, A and Rao, W and Chan, PWH
Keywords:	gold catalysis, mechanistic study, acyl migration, epoxidation, Density Functional Theory, carbocyclic synthesis, cyclization, gold, homogenous catalysis, synthetic methods
Journal or Publication Title:	Advanced Synthesis and Catalysis
Publisher:	Wiley-V C H Verlag Gmbh
ISSN:	1615-4150
DOI / ID Number:	10.1002/adsc.201901263
Copyright Information:	Copyright 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Related URLs:	Google Scholar: Ariafard, A UTAS Profile: Ariafard, A
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