Stereoselective synthesis of cis- or trans-2,4-disubstituted butyrolactones from Wynberg lactone

Stereoselective synthesis of cis- or trans-2,4-disubstituted butyrolactones from Wynberg lactone

(R)-Wynberg lactone was used to prepare various asymmetric 2,4-disubstituted butyrolactones in three to four steps. Attainment of any possible stereoisomer, based upon commencement from (R)- or (S)-4-trichloromethyl-2-oxetanone, and the capacity to install disparate substituents at C2 make this appr...

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Veröffentlicht in:Tetrahedron 2012-07, Vol.68 (27-28), p.5396-5405
Hauptverfasser: Ganta, Ashok, Shamshina, Julia L., Cafiero, Lauren R., Snowden, Timothy S.
Format: Artikel
Sprache:eng
Schlagworte:
Asymmetry
Butyrolactone
Chemistry
Exact sciences and technology
gem-Dichloroepoxide
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lactones
Organic chemistry
Preparations and properties
Synthesis
Tetrahedrons
Trichloromethyl carbinol
Wynberg lactone
β-Lactone
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Zusammenfassung:(R)-Wynberg lactone was used to prepare various asymmetric 2,4-disubstituted butyrolactones in three to four steps. Attainment of any possible stereoisomer, based upon commencement from (R)- or (S)-4-trichloromethyl-2-oxetanone, and the capacity to install disparate substituents at C2 make this approach particularly versatile. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.04.107