Asymmetric Homoenolate Additions to Acyl Phosphonates through Rational Design of a Tailored N-Heterocyclic Carbene Catalyst

Asymmetric Homoenolate Additions to Acyl Phosphonates through Rational Design of a Tailored N-Heterocyclic Carbene Catalyst

A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.

Jang, K. P.; Hutson, G. E.; Johnston, R. C.; McCusker, E. O.; Cheong, P. H.-Y.; Scheidt, K. A. J. Am. Chem. Soc. 2013, Article ASAP. DOI: 10.1021/ja410932t