Abstract
Kinetic resolution of nitroallylic amines was established using chiral α,α-l-diphenylprolinol silyl ether auxiliary through isolation of the dihydrooxazine N-oxide intermediates. Further hydrolyzing the resting states provided tetrahydropyridines in high chemical yields and high to excellent stereoselectivities (up to >20:1 dr and 98% ee). A detailed mechanistic explanation for stereoselective protonation in the dihydrooxazine was probed computationally. In addition, the probable intermediates in α-halogenation of aldehydes (masked with enamines) were isolated to provide crystallographic evidence.
| Original language | English |
|---|---|
| Pages (from-to) | 3046-3049 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 18 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - 2016 Jul 1 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Fingerprint Dive into the research topics of 'Dihydrooxazine N-Oxide Intermediates as Resting States in Organocatalytic Kinetic Resolution of Functionalized Nitroallylic Amines with Aldehydes'. Together they form a unique fingerprint.
Cite this
Gurubrahamam, R., Chen, Y. M., Huang, W. Y., Chan, Y. T., Chang, H. K., Tsai, M. K., & Chen, K. (2016). Dihydrooxazine N-Oxide Intermediates as Resting States in Organocatalytic Kinetic Resolution of Functionalized Nitroallylic Amines with Aldehydes. Organic Letters, 18(13), 3046-3049. https://doi.org/10.1021/acs.orglett.6b00493