Open AccessGold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes
Author(s) -
Ryan J. Felix,
Osvaldo Gutiérrez,
Dean J. Tantillo,
Michel R. Gagné
Publication year - 2013
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo400139g
Subject(s) - bicyclic molecule , catalysis , tricyclic , transformation (genetics) , chemistry , stereochemistry , computational chemistry , combinatorial chemistry , organic chemistry , biochemistry , gene
Gold(I) catalysts effectively promote the Cope rearrangement of acyclic 1,5-dienes bearing a terminal cyclopropylidene. When this methodology is applied to cyclic substrates an unexpected transformation occurs, resulting in the formation of a tricyclic compound incorporating a bicyclo[4.2.0]oct-1-ene core, a portion of which is found in a number of natural products. Density functional theory calculations (M06 and M06-2X) reveal insight into the mechanism and thermodynamics of this unique transformation.