Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes | Zendy

Ryan J. Felix | Zendy; Osvaldo Gutiérrez | Zendy; Dean J. Tantillo | Zendy; Michel R. Gagné | Zendy

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Gold(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 -

the 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) - chemistry , bicyclic molecule , catalysis , tricyclic , transformation (genetics) , stereochemistry , computational chemistry , organic chemistry , gene , biochemistry

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.

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