The traditional Staudinger/aza-Wittig reaction represents one of the most powerful tools for imine formation. However, this multistep procedure, sacrificial phosphine has to be used, resulting in difficulties purification process and waste disposal at same time. Here, we report a redox-neutral azide–alcohol imination methodology enabled by base-metal nickel PN3 pincer catalyst. one-step, waste-...

The first enantioselective synthesis of palinurin has been accomplished starting from commercially available furaldehyde and (R)-methyl-3-hydroxy-2-methylpropionate; the key steps of the synthesis include the use of a chiral pyrrolidine to create the chiral tetronic moiety, and Horner-Wadsworth-Emmons, Wittig and Wittig-Horner reactions to construct the alkene units.

The mechanism of the Wittig reaction of anisaldehyde with a stabilized ylide was studied by a combination of (13)C kinetic isotope effects, conventional calculations, and molecular dynamics calculations in a cluster of 53 THF molecules. The isotope effects support a cycloaddition mechanism involving two sequential transition states associated with separate C-C and P-O bond formations. However, ...

Asymmetric synthesis of drug-like functionalized spiro[chroman-3,3'-indolin]-2'-ones 5 containing three contiguous stereocenters with high diastereo- and enantioselectivities was achieved using the reflexive-Michael (r-M) reaction of unmodified hydroxyenals 1 with various (E)-3-alkylideneindolin-2-ones 2 in the presence of (R)-DPPOTMS/AcOH (R)-3/4b as a catalyst at room temperature. Chiral spir...

The citrus mealybug, is a cosmopolitan pest and affects many crops. The female sex pheromone has been identified by Bierl-Leonhardt et al., in 1981 as (+)-(1R)-cis-2,2-dimethyl-3isopropenylcyclobutanemethanol acetate 1. Several groups including our team have synthesized the pheromone. A number of analogs have also been prepared in order to study the structure-activity relationship. We present h...