VCD configuration of enantiopure/-enriched tetrasubstituted alpha-fluoro cyclohexanones and their use for epoxidation of trans-olefins

Chirality
Teresa B FreedmanL Bouerat

Abstract

The configurations of three enantiopure tetrasubstituted alpha-fluoro cyclohexanones (-)-5Ia, (-)-5IIa and (-)-6a were determined by VCD and proved to be (-)-(2S,5R)-5Ia, (-)-(2R,5R)-5IIa, and (-)-(2R,5R)-6a. The VCD study also identified the conformers populated in CDCl3 solution, including higher-energy gas-phase conformers with equatorial fluorine for 5Ia and 5IIa that are stabilized in CDCl3 solution. Used as catalysts for epoxidation of trans olefins (beta-methylstyrene, stilbene, methyl p-methoxy cinnamate) by oxone, it was found that (-)-5Ia is the most efficient for all trans olefins (providing, respectively, 62%, 90% and 66% ee) but that all three ketones provide high ee% with stilbene (78-90% ee). Moreover, the configurations predicted from the stereo outcome of the epoxidation reaction are identical to those determined by VCD.

References

May 9, 2003·Bioorganic & Medicinal Chemistry·Bruce E MaryanoffVictor W Day

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Citations

Oct 27, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Sergio AbbateRenzo Ruzziconi
May 1, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Mohammad Reza PoopariYunjie Xu
Apr 16, 2020·Journal of Asian Natural Products Research·Ming-Feng ZouSheng Yin
Dec 1, 2017·Natural Product Research·Wilart PompimonNarong Nuntasaen

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