Refine
Has Fulltext
- no (2)
Year of publication
- 2011 (2) (remove)
Document Type
- Article (2)
Language
- English (2) (remove)
Is part of the Bibliography
- yes (2)
Keywords
- Lactones (2) (remove)
Institute
- Institut für Chemie (2) (remove)
A protected derivative of (3R, 4R)-hexa-1,5-diene-3,4-diol, a conveniently accessible C-2-symmetric building block, undergoes single or double cross metathesis with methyl acryl-ate. The cross metathesis products are amenable to stereoselective conjugate addition reactions and can be converted into either gamma-butyrolactones or gamma-lactams.
Butenolides, obtained by ring-closing metathesis (RCM) of acrylates, undergo quantitative deprotonation with amide bases. Trapping of the resulting anions with electrophiles, for example, chlorophosphates, give furans. Subsequent DielsAlder reaction and acid-catalysed rearrangement of the resulting oxabicyclonorbornadienes give substituted benzenes.