88722-76-3Relevant academic research and scientific papers
Synthetic Opportunities Offered by Anti α-Methylene-β-hydroxy-γ-alkoxy Esters: Stereoselective Reactions at the Double Bond
Bernardi, Anna,Beretta, Maria Grazia,Colombo, Lino,Gennari, Cesare,Poli, Giovanni,Scolastico, Carlo
, p. 4442 - 4447 (2007/10/02)
Addition of tert-butyl β-(dimethylamino)propionate to (S)-O-lactaldehyde and (R)-2,3-O-isopropylideneglyceraldehyde gave, after N-methylation and elimination α-methylene-β-hydroxy-γ-alkoxy esters in fairly good yield (40-60percent) and a high anti-syn ratio (7-12:1).These esters were easily lactonized, by acidic treatment, to the corresponding α-methylene-β-hydroxy-γ-butyrolactones.The double bond of these compounds was submitted to various reactions (cuprate addition, reduction, dihydroxylation).The stereoselectivity of these reactions was studied and ranged from poor to good depending on the specific substrate and reaction used.Acyclic substrates proved to be more selective than the corresponding γ-lactones.The stereoconfiguration of the products was assigned by comparison to known compounds (blastmycinolactol-a, epi-D-hamamelose).
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.
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 (2007/10/02)
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.
