Catalytic
Enantioselective [3 + 2] Cycloaddition of
α‑Keto Ester Enolates and Nitrile Oxides
Posted on 2017-06-05 - 00:00
An
enantioselective [3 + 2] cycloaddition reaction between nitrile
oxides and transiently generated enolates of α-keto esters has
been developed. The catalyst system was found to be compatible with
in situ nitrile oxide-generation conditions. A versatile array of
nitrile oxides and α-keto esters could participate in the cycloaddition,
providing novel 5-hydroxy-2-isoxazolines in high chemical yield with
high levels of diastereo- and enantioselectivity. Notably, the optimal
reaction conditions circumvented concurrent reactions via O-imidoylation
and hetero-[3 + 2] pathways.
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Bartlett, Samuel
L.; Sohtome, Yoshihiro; Hashizume, Daisuke; White, Peter S.; Sawamura, Miki; Johnson, Jeffrey S.; et al. (2017). Catalytic
Enantioselective [3 + 2] Cycloaddition of
α‑Keto Ester Enolates and Nitrile Oxides. ACS Publications. Collection. https://doi.org/10.1021/jacs.7b03782
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AUTHORS (7)
- SBSamuel L. BartlettYSYoshihiro SohtomeDHDaisuke HashizumePWPeter S. WhiteMSMiki SawamuraJJJeffrey S. JohnsonMSMikiko Sodeoka
