An organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols via Michael/acetalization sequence to give fully substituted tetrahydropyranols is described. The process affords the products with high to excellent stereoselectivities (up to 19.9:1.5:1 dr and 98% ee). The highly enantioenriched, less reactive (S)-nitroallylic alcohols 3 were isolated with good to high chemical yields (30-44%). The synthetic application of the resolved substrate is shown toward the synthesis of enantioenriched (+)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
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Gurubrahamam, R. (Contributor), Chen, K. (Contributor) & Cheng, Y. (Contributor), Unknown Publisher, 2015 Feb 6
Chen, K. (Contributor), Chen, K. (Contributor), Roy, S. (Contributor), Cheng, Y. (Contributor) & Gurubrahamam, R. (Contributor), Unknown Publisher, 2015 Feb 6