95636-68-3Relevant articles and documents
Stereoelectronic and solvent effects on the allylic oxyfunctionalization of alkenes with singlet oxygen
Alberti, Mariza N.,Orfanopoulos, Michael
, p. 10660 - 10675 (2007/10/03)
The factors that control the stereochemistry of sensitized photooxygenation of alkenes via singlet oxygen (ene reaction) are selectively reported. We also introduce our most recent stereoelectronic effects on the singlet oxygen-ene reaction. The origin of
SYNTHESE STEREOSELECTIVE D'ESTERS α,β-ETHYLENIQUES α-METHYLES Z OU E PAR LA REACTION DE WITTIG-HORNER A PARTIR DE PHOSPHONATES OU D'OXYDES DE PHOSPHINE
Etemad-Moghadam, Guita,Seyden-Penne, Jacqueline
, p. 5153 - 5166 (2007/10/02)
The reaction of α-branched aldehydes with diethyl 1-carbomethoxyethyl phosphonate 1b in THF/nBuLi at low temperature leads stereoselectively to Z α-methyl α,β-unsaturated esters.From a linear aldehyde, the reaction is less stereoselective, while from α,β-unsaturated ones, the E isomers are predominantly formed in good yields.From diphenyl 1-carbomethoxyethyl phosphine oxide 2b, E α-methyl α,β-unsaturated esters are stereoselectively formed either in DMF/tBuOK or in phase transfer conditions, whatever the starting aldehyde is, also in good yields.This reagent can thus advantageously replace the corresponding P-ylid.In all cases, the reaction conditions are determined so that by-products formation is minimized.
