116491-07-7Relevant academic research and scientific papers
Iterative synthesis of deoxypropionate units: The inductor effect in acyclic conformation design
Hanessian, Stephen,Chahal, Navjot,Giroux, Simon
, p. 7403 - 7411 (2007/10/03)
Conjugate addition of lithium dimethylcuprate to acyclic α,β-unsaturated esters of varying lengths bearing terminal alkyl or phenyl groups leads to a preponderance of syn 1,3-adducts when one methyl is already present. Conversion to enoates, and iteration of cuprate additions also favors syn adducts to give contiguous deoxypropionate units in a growing chain. The effect of end-group variation (Me, i-Pr, phenyl, tert-butyl) in conjunction with the nature of the ester group (Me, tert-butyl, etc.) on the diastereoselectivity of syn and anti products was studied. The results are rationalized in terms of inductor effects related to the minimization of the 1,5-pentane interactions in energetically favored folded conformations and corroborated by homodecoupling NMR studies.
CATALYTIC OSMYLATION OF ELECTRON POOR ALLYLIC ALCOHOLS AND ETHERS. A SYNTHETIC APPROACH TO BRANCHED CHAIN SUGARS
Bernardi, Anna,Cardani, Silvia,Scolastico, Carlo,Villa, Roberto
, p. 491 - 502 (2007/10/02)
The catalytic osmylation of electron-poor allylic ethers and alcohols was studied.In the case of γ-alkoxy E-enoates reaction selectivity was found to range from 2:1 to 8:1 in favor of the arabino (2,3-syn - 3,4-anti) product, regardless of the double bond
