161344-89-4

Upstream product

• 161344-86-1 ethyl 3E-<(1R,2S)-2-phenyl-1-cyclopropyl>prop-1-enoate 
• 14371-10-9 (E)-3-phenylpropenal 
• 34271-30-2 (1S,2S)-2-phenylcyclopropane-1-carbaldehyde 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Relevant academic research and scientific papers

Studies on the diastereoselective preparation of bis-cyclopropanes

The identification of two natural products, FR-900848 and U-106305, has stimulated interest concerning the relationship between configurational isomerism, conformational isomerism, and biological activity of polycyclopropanes. Efforts to investigate the relationship between configurational and conformational isomerism through molecular modeling suggest that significantly different three-dimensional structures will result from unique primary structures. Any effort to address these issues demands that stereoselective methods for the preparation of polycyclopropanes be developed. We have investigated the application of zinc-carbenoid cyclopropanation in the presence of chiral dioxaboralanes to the preparation of eight stereochemically unique bicyclopropanes. The frans-vinylcyclopropane starting materials demonstrated very little substrate-induced stereoselectivity, while the cis-vinylcyclopropane demonstrates modest to excellent stereocontrol. A model for the substrate-based stereocontrol is proposed. We also used the spectroscopic data gathered in this investigation to probe the substrate-mediated stereocontrol in the rhodium(II)-catalyzed cyclopropanation of vinylcyclopropanes with ethyl diazoacetate.

Asymmetric synthesis of bicyclopropane derivatives

Both syn- and anti-bicyclopropane derivatives have been efficiently prepared with good relative and absolute stereocontrol using reagent controlled asymmetric cyclopropanation reactions. Double Simmons-Smith cyclopropanation of 2,4-dien-1-ols stereoselectively gave the corresponding anti-bicyclopropane derivatives.

Approaches to the assembly-of the antifungal agent FR-900848: Studies on the asymmetric synthesis of bicyclopropanes and an X-ray crystallographic analysis of (4R,5R)-2-[(1R,3S,4S,6R)-6-phenyl-1-bicyclopropyl]-1,3- dimethyl-4,5-diphenylimidazolidine

Both syn- and anti-bicyclopropane derivatives are efficiently prepared with good relative and absolute stereocontrol; structures are unequivocally determined by an X-ray crystallographic study of the title imidazolidine-derivative.