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Ti(III)-mediated opening of 2,3-epoxy alcohols to build five-membered carbocycles with multiple chiral centres |
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| Authors: | Midde SreekanthGavinolla Pranitha Bharatam JagadeeshTushar Kanti Chakraborty |
| Institution: | a Indian Institute of Chemical Technology, CSIR, Hyderabad 500 607, India b Centre for Nuclear Magnetic Resonance, Indian Institute of Chemical Technology, CSIR, Hyderabad 500 607, India c Central Drug Research Institute, CSIR, Lucknow 226 001, India |
| 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. |
| Keywords: | Epoxide opening Ti(III) Iridoids Carbocyclization Free radicals Sharpless kinetic resolution |
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