Reductive generation of active zero-valent in SnCl2Al system and its use for highly diastereoselective reaction of cinnamyl chloride and aldehydes.
✍ Scribed by Kenji Uneyama; Hiromi Nanbu; Sigeru Torii
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 114 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Highly diastereoselective reaction of cinnamyl chloride with aldehydes was achieved by the use of active zero-vale& tin generated in SnC12-Al system. Reactions of the well-designed allylic organometallics of silicon, chromium, boron, and etc with aldehydes provide the corresponding homoallylic alcohols with high diastereoselectivity'). Not only the high stereoselectivity and yield, but also a facile synthetic procedure are essential for any feasible synthetic methodologies. Recent Coxon's communication2) on the Sn-A13) mediated diastereoselective reaction of cinnamyl chloride with
aldehydes has prompted us to describe our simple method on SnC12-Al system which creates a higher reactivity along with complete diastereocontrol and high yield in a neutral medium.