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Gold catalyzed cyclopropanation/[5+3] cycloaddition of 1,4,9- and 1,4,10-allenenynes to bicyclo[3.3.1]nonane derivatives

Chen, X, Zhou, Y, Jin, J, Farshadfar, K, Ariafard, A ORCID: 0000-0003-2383-6380, Rao, W and Chan, PWH 2019 , 'Gold catalyzed cyclopropanation/[5+3] cycloaddition of 1,4,9- and 1,4,10-allenenynes to bicyclo[3.3.1]nonane derivatives' , Advanced Synthesis and Catalysis , pp. 1-13 , doi: 10.1002/adsc.201901263.

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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

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