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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

journal contribution
posted on 2023-05-20, 11:20 authored by Chen, X, Zhou, Y, Jin, J, Farshadfar, K, Alireza AriafardAlireza Ariafard, Rao, W, Chan, PWH
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.

Funding

Australian Research Council

University of Wollongong

History

Publication title

Advanced Synthesis and Catalysis

Pagination

1-13

ISSN

1615-4150

Department/School

School of Natural Sciences

Publisher

Wiley-V C H Verlag Gmbh

Place of publication

Po Box 10 11 61, Weinheim, Germany, D-69451

Rights statement

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

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences