Sreekanth, Midde ; Pranitha, Gavinolla ; Jagadeesh, Bharatam ; Chakraborty, Tushar Kanti (2011) Ti(III)-mediated opening of 2,3-epoxy alcohols to build five-membered carbocycles with multiple chiral centres Tetrahedron Letters, 52 (14). pp. 1709-1712. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2011.02.001
Abstract
Stereoselective construction of highly substituted five-membered carbocycles with multiple chiral centres is described. Sharpless kinetic resolution was applied as the key step to prepare the required 2,3-epoxy alcohols and a Ti(III) radical mediated opening of the epoxide ring followed by intramolecular trapping of the generated radical with a suitably placed α,β-unsaturated ester resulted in the formation of five-membered carbocycles with up to three consecutive new chiral centres stereoselectively fixed.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Epoxide Opening; Ti(III); Iridoids; Carbocyclization; Free Radicals; Sharpless Kinetic Resolution |
| ID Code: | 69573 |
| Deposited On: | 14 Nov 2011 03:53 |
| Last Modified: | 14 Nov 2011 03:53 |
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