Efficient asymmetric synthesis of chiral hydroxy-gamma-butyrolactones.
Treatment of beta-vinyl-beta-hydroxy-N-acyloxazolidin-2-ones with VO(acac)(2) and tert-butyl hydroperoxide results in formation of unstable epoxides that are ring-opened by intramolecular nucleophilic attack of their exocyclic carbonyl fragments to afford highly functionalized trisubstituted hydroxy-gamma-butyrolactones in >95% de, with a polymer-supported oxazolidin-2-one having been used to transfer this methodology to the solid phase.
Davies
Iwan R
IR
Department of Chemistry, University of Bath, BA2 7AY, UK.
Cheeseman
Matt
M
Green
Rachel
R
Mahon
Mary F
MF
Merritt
Andrew
A
Bull
Steven D
SD
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism
D023303:Oxazolidinones; D015107:4-Butyrolactone