Origin of stereoselectivity in the imidazolidinone-catalyzed reductions of cyclic alpha,beta-unsaturated ketones. Academic Article

abstract

• The organocatalytic transfer hydrogenation reactions of 3-phenyl-2-cyclopentenone with imidazolidinone catalysts are evaluated using the hybrid density functional (B3LYP/6-31G(d)) theory. The origin of the preference for the (E) iminium transition state is determined, and the stereoselectivity of hydride transfer is investigated.

authors

• Gutierrez Santacruz, Osvaldo

published proceedings

• Org Lett

author list (cited authors)

• Gutierrez, O., Iafe, R. G., & Houk, K. N.

citation count

• 40

complete list of authors

• Gutierrez, Osvaldo||Iafe, Robert G||Houk, KN

publication date

• January 2009

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Catalysis
• Computer Simulation
• Cyclopentanes
• Hydrogenation
• Imidazolidines
• Ketones
• Models, Chemical
• Molecular Structure
• Oxidation-Reduction
• Stereoisomerism

PubMed Central ID

• 19722547

Digital Object Identifier (DOI)

• 10.1021/ol901586t

start page

• 4298

end page

• 4301

volume

• 11

issue

• 19

URL

• http://dx.doi.org/10.1021/ol901586t