Journal
ORGANIC LETTERS
Volume 16, Issue 19, Pages 5104-5107Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol502454r
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Funding
- University of Southampton
- AstraZeneca
- Higher Committee for Education Development in Iraq
- Eli Lilly
- EPSRC
- European Regional Development Fund (ERDF, ISCE-Chem & INTERREG IVa program) [4061]
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The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing different chiral auxiliaries was investigated, leading to the discovery of trans-2-tritylcyclohexanol (TTC) as a highly effective chiral controller for the formation of the 2,5-substituted THF diol product with high diastereoselectivity (d(r) similar to 97:3). Chiral resolution of (+/-)-TTC, prepared in one step from cyclohexene oxide, afforded (-)-(1S,2R)-TTC (er >99:1), which was applied to the synthesis of (+)-trans-(2S,5S)-linalool oxide.
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