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Chemoenzymatic synthesis of optically active γ-alkyl-γ-butenolides
- Source :
- Tetrahedron: Asymmetry. 17:2292-2298
- Publication Year :
- 2006
- Publisher :
- Elsevier BV, 2006.
-
Abstract
- rac-Hept-1-en-3-ol 4 was subjected to an enantioselective esterification in the presence of Novozyme 435 and vinyl crotonate as the acyl donor to give (3S)-oct-1-en-3-yl crotonate 7 in >99% ee and (3R)-alcohol 4 in 99% ee. The E-value of this enzymatic reaction was found to be >1000. The (S)-crotonic ester 7 was converted by ring-closing metathesis (RCM) using Grubbs’ catalyst to give (S)-oct-2-en-4-olide 1 in 96% yield while keeping the high enantiomeric excess.
Details
- ISSN :
- 09574166
- Volume :
- 17
- Database :
- OpenAIRE
- Journal :
- Tetrahedron: Asymmetry
- Accession number :
- edsair.doi...........6c589844e80a254cb58485abf0989f74