292081-22-2

Upstream product

• 100-52-7 benzaldehyde 
• 191658-67-0 2-((1R,2S,6R,7S)-1,10,10-Trimethyl-2-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.0^2,6]dec-4-ylmethyl)-acrylic acid ethyl ester 

Relevant academic research and scientific papers

Enantioselective addition of β-functionalized allylboronates to aldehydes and aldimines. Stereocontrolled synthesis of α-methylene-γ-lactones and lactams

We report results regarding the development of condensations of chiral β-alkoxycarbonylallylboronates on aldehydes and imines. These allylboronates add in a highly enantioselective and diastereospecific manner to afford biologically and synthetically useful chiral α-methylene-γ-butyrolactones and lactams. The nature of the electrophile (aldehyde vs imine) is shown to have a dramatic influence on the mechanism of the reaction, probably directing the stereoselectivity of the process through different transition states.