Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 430-433 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 17 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2015 Feb 6 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Gurubrahamam, R., Cheng, Y. S., & Chen, K. (2015). Control of five contiguous stereogenic centers in an organocatalytic kinetic resolution via michael/acetalization sequence: Synthesis of fully substituted tetrahydropyranols. Organic Letters, 17(3), 430-433. https://doi.org/10.1021/ol5033656