Abstract
The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes was established. The reaction was successfully achieved by using (R,R)-SalenAlCl as the chiral catalyst and LiI as an additive at 0°C in dichloromethane. Moderate to good yields and up to 62% ee were obtained. The new system showed a good substrate scope in which both aromatic aldehydes and aliphatic aldehydes can be employed. The reaction provided the first catalytic and enantioselective approach to chiral β-iodo Baylis-Hillman ester adducts.
| Original language | English |
|---|---|
| Pages (from-to) | 1757-1762 |
| Number of pages | 6 |
| Journal | Tetrahedron Asymmetry |
| Volume | 16 |
| Issue number | 10 |
| DOIs | |
| State | Published - May 23 2005 |
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Chen, D., Guo, L., Kotti, S. R. S. S., & Li, G. (2005). The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes by using chiral salen catalyst. Tetrahedron Asymmetry, 16(10), 1757-1762. https://doi.org/10.1016/j.tetasy.2005.03.038