Gold(I)-catalyzed formation of bicyclo[4.2.0]oct-1-enes. Academic Article

abstract

• 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.

authors

• Gutierrez Santacruz, Osvaldo

published proceedings

• J Org Chem

author list (cited authors)

• Felix, R. J., Gutierrez, O., Tantillo, D. J., & Gagn, M. R.

citation count

• 22

complete list of authors

• Felix, Ryan J||Gutierrez, Osvaldo||Tantillo, Dean J||Gagné, Michel R

publication date

• January 2013

publisher

• American Chemical Society (ACS)  Publisher

published in

• Journal of Organic Chemistry  Journal

keywords

• Bridged Bicyclo Compounds
• Catalysis
• Molecular Structure
• Organogold Compounds
• Quantum Theory

PubMed Central ID

• 23663099

Digital Object Identifier (DOI)

• 10.1021/jo400139g

start page

• 5685

end page

• 5690

volume

• 78

issue

• 11

URL

• http://dx.doi.org/10.1021/jo400139g