Abstract
The asymmetric conjugate addition of arylboronic acids to N-phthalimidodehydroalanine 1i catalyzed by Rh(I)/L1a enables the facile preparation of chiral functionalized phenylalanines. The reaction proceeds by a conjugate addition and enantioselective protonation cascade, affording a rhodium enolate that undergoes re-face protonation. The reaction tolerates various arylboronic acids and can be used in the gram-scale synthesis of (S)-phenylalanine hydrochloride, demonstrating the reaction scope and the synthetic feasibility of the process.
| Original language | English |
|---|---|
| Pages (from-to) | 9468-9472 |
| Number of pages | 5 |
| Journal | Organic Letters |
| Volume | 21 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 2019 Dec 6 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Cite this
Jian, J. H., Zeng, H. W., Kuo, T. S., Wu, P. Y., & Wu, H. L. (2019). Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade. Organic Letters, 21(23), 9468-9472. https://doi.org/10.1021/acs.orglett.9b03666