1192-42-3Relevant academic research and scientific papers
Enantioselective syntheses of substituted γ-butyrolactones
Eliel, Ernest L.,Bai, Xu,Ohwa, Masaki
, p. 63 - 70 (2007/10/03)
The previously described chiral 2-acyloxathianes 5 (Scheme I) are used in two different enantioselective syntheses of γ-butyrolactones. In one synthesis, Grignard addition, cleavage and reduction to carbinols RR'C(OH)CH2OH is followed by tosylation, malonate homologation, lactonization, and removal of the carbomethoxy group to give optically active γ-lactones. A modification of this synthesis (Scheme I) leads to optically active α-methylene-γ-lactones. In the second synthesis, reaction of a bromomagnesium enolate with ketones 5 leads to β-hydroxyesters, which, by appropriate sequences of reduction and cleavage (Scheme II) are converted to optically active α- or β-hydroxy-γ-lactones.
Asymmetric synthesis of α-alkyl-α-hydroxy-γ-butyrolactones
Pansare, Sunil V.,Jain, Rajendra P.,Ravi, R. Gnana
, p. 3103 - 3106 (2007/10/03)
A new enantioselective approach to α-alkyl-α-hydroxy-γ-butyrolactones employing (1R,2S)-ephedrine-derived chiral allyl morpholinones as starting materials is described.
Preparation of α-Hydroxy-γ-lactones and their Application in the Synthesis of α,β-Butenolides, α-Alkylidene-γ-lactones and Furans
Munoz, A. Heber,Tamariz, Joaquin,Jimenez, Rogelio,Mora, Gustavo Garcia de la
, p. 501 - 522 (2007/10/02)
A straightforward synthesis of α-hydroxy-γ-butyrolactones was carried out by condensation reaction of the lithium anion of ethoxyethyl-protected cyanohydrins with epoxides, followed by acidic treatment.Synthetic applications of these synthons in the preparation of interesting α,β-butenolides, α-alkylidene-γ-lactones and furans are described.
