A highly stereoselective conversion of α-allenic alcohols to syn-1,2-diol derivatives
✍ Scribed by Richard W. Friesen; André Giroux
- Publisher
- Elsevier Science
- Year
- 1993
- Tongue
- French
- Weight
- 292 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
A new route to enantiopure syn and anti 1,2-diols is described from oxalyl-di-(Nmethyl-N-methoxyamide) via the corresponding ~-ketosulfoxide. This is the first report of the stereoselective reduction ofaT--keto-~-hydroxysulfoxide.
The a-alkoxyallylstannane dicobalt hexacarbonyl alkynal complex 18 afforded the cyclododecadienyne alcohol complex 19 as a single diastereoisomer in 70% yield upon treatment with BF3 l Et20 at -78°C. The reaction is thought to proceed by prior isomerization to the y-alkoxyallylstannane.
The stereoselective addition of the 2-hydroxyl group of glucose to the mercurated vinyl group of 2-alkenyl glycosides followed by hydride reduction and removal of the saccharide fragment was used to prepare enantiomerically pure 1,2-dihydroxy alkanes. Diols of (R) or (S) configuration can be synthes