Abstract
The unprecedented development of asymmetric Rh-catalyzed 1,2-allylation of N-Ts- and N-Ns-aldimines is achieved. This protocol utilizes potassium allyltrifluoroborates and various aldimines to generate enantioenriched homoallylic amines in the presence of 3.0 mol % of Rh(I)/L1b catalyst with up to 90% yield, 98% ee (R = H), and 10:1 diastereoselectivity (R = Me or Ph), yielding the same major diastereomer when using potassium (E)- and (Z)-crotyltrifluoroborate. Its synthetic utility is also illustrated in the total synthesis of (-)-crispine A.
| Original language | English |
|---|---|
| Pages (from-to) | 158-161 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 20 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2018 Jan 5 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Chiang, P. F., Li, W. S., Jian, J. H., Kuo, T. S., Wu, P. Y., & Wu, H. L. (2018). Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines: Total Synthesis of (-)-Crispine A. Organic Letters, 20(1), 158-161. https://doi.org/10.1021/acs.orglett.7b03523