88722-84-3Relevant academic research and scientific papers
Stereoselective Synthesis of α-Methylene-β-hydroxy-γ-alkoxy Esters from α-Alkoxy Aldehydes
Banfi, Luca,Colombo, Lino,Gennari, Cesare,Scolastico, Carlo
, p. 1112 - 1113 (1983)
The Reformatsky-type condensation between methyl and t-butyl 3-(N,N-dimethylamino)propionates (9) and (10) with α-alkoxy aldehydes, which has been studied on varying the protective group of the aldehyde, proceeds with good diastereoselectivity.
High Diastereoface Selection in an Ester Enolate Addition to α-Alkoxy Aldehydes: Stereoselective Synthesis of α-Methylene-β-hydroxy-γ-alkoxy Esters
Banfi, Luca,Bernardi, Anna,Colombo, Lino,Gennari, Cesare,Scolastico, Carlo
, p. 3784 - 3790 (2007/10/02)
The aldol-type condensation of β-(dimethylamino)propionates 3 and 4 with a series of α-alkoxy aldehydes proceeds with unprecedented high stereoselectivity (up to 24:1) to give anti α-methylene-β-hydroxy-γ-alkoxy esters.The best results were obtained when the reaction was carried out in diethyl ether and the ester enolate was allowed to equilibrate to the thermodynamically more stable geometric isomer.
