92735-41-6Relevant 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.
Synthesis of (R)-2,3-Dihydro-2,5-dimethyl-2-isopropylfuran
Bai, Xu,Eliel, Ernest L.
, p. 2086 - 2089 (2007/10/02)
The synthesis of (R)-2,3-dihydro-2,5-dimethyl-2-isopropylfuran (1), an insect pheromone, via a 1,3-oxathiane is reported.Key steps are the preparation of (S)-2,3-dimethylbutane-1,2-diol (7) from isobutyryloxathiane 5 and reaction of lithiated acetone dimethylhydrazone with tosylated diol 8.NMR spectra of the key tautomeric precursors, 2/2'/3, to 1 have been analyzed in detail, and the enantiomeric excess of these precursors was determined by a chiral shift 13C NMR experiment.
PHEROMONE SYNTHESIS-63 SYNTHESIS OF BOTH THE ENANTIOMERS OF 2,3-DIHYDRO-2-ISOPROPYL-2,5-DIMETHYLFURAN, A SEX SPECIFIC COMPOUND IN FEMALES OF THE BEETLE HYLECOETUS DERMESTOIDES L
Mori, Kenji,Ebata, Takashi,Takechi, Shozo
, p. 1761 - 1766 (2007/10/02)
Both the enantiomers of 2,3-dihydro-2-isopropyl-2,5-dimethylfuran were synthesized employing the Sharpless asymmetric epoxidation reaction.The (R)-(-)-enantiomer of this cyclic enol ether was also synthesized from (R)-(-)-linalool.
