Diastereoselectivity in the directed aldol condensation of 2-trimethylsiloxyfuran with aldehydes. A stereodivergent route to threo and erythro δ-hydroxy-γ-lactones
✍ Scribed by Charles W. Jefford; Danielle Jaggi; John Boukouvalas
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 247 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Threo and erythro-6-hydroxy-a,fi-unsaturated -y-lactones are obtained with useful diastereoselection by condensing 2-trimethylsiloxyfuran and aldehydes by varying the reaction reaction conditions.
A stereomechanistic rationale is presented together with a practical two-step synthesis of the threo and erythro 5-hydroxy-4-decanolides (L factors).
Recent reports on 2-trimethylsiloxyfuran (1) show that it has promise as a masked butenolide.lm4 However, in order to exploit 1 in synthesis, the appropriate conditions need to be found for controlling the regio-and diastereoselectivity of carbon-carbon bond formation.
Described herein are results of a systematic investigation of the reaction of 1 with aldehydes which demonstrate for the first time how useful diastereoselection can be achieved at will for obtaining predominantly either threo (2) or erythro (4) 6-hydroxy-a,j3-unsaturated-ylactones.