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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

Citation

Chen, X and Zhou, Y and Jin, J and Farshadfar, K and Ariafard, A and Rao, W and Chan, PWH, 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. ISSN 1615-4150 (2019) [Refereed Article]

Copyright Statement

Copyright 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

DOI: doi:10.1002/adsc.201901263

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 Details

Item Type:Refereed Article
Keywords:gold catalysis, mechanistic study, acyl migration, epoxidation, Density Functional Theory, carbocyclic synthesis, cyclization, gold, homogenous catalysis, synthetic methods
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Physical Organic Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
UTAS Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:137656
Year Published:2019
Funding Support:Australian Research Council (DP180100904)
Deposited By:Chemistry
Deposited On:2020-02-25
Last Modified:2020-03-11
Downloads:0

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