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Gold‐Catalyzed Double Cycloisomerization of 1‐Ene‐4,10‐diynyl Esters to Bicyclo[6.3.0]undeca‐2,4,9‐trienyl Esters
Author(s) -
Mathiew Mitch,
Tan Javey Khiapeng,
Chan Philip Wai Hong
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201809376
Subject(s) - cycloisomerization , bicyclic molecule , enyne , chemistry , hydride , stereochemistry , cyclopropene , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry , hydrogen
Abstract A synthetic method to prepare bicyclo[6.3.0]undeca‐2,4,9,trienyl esters efficiently from gold(I)‐catalyzed Rautenstrauch rearrangement/1,5‐hydride shift/8‐ endo ‐ dig cyclization of 1‐ene‐4,10‐diynyl esters is described. The suggested double cycloisomerization mechanism delineates the first example of an unactivated all‐carbon tethered 1,7‐enyne, either preformed or formed in situ, which undergoes an 8‐ endo ‐ dig cyclization pathway to give a cyclooctane motif. It also offers an extremely rare synthetic method in organic chemistry that can sequentially assemble both ring components of the bicyclic motif from an acyclic precursor in one step.