Rapid, highly diastereoselective addition of dialkylzinc reagents to atropisomeric 2-formyl arylamides |
| |
| Authors: | Ciril Jimeno |
| |
| Affiliation: | Contribution from Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323, USA |
| |
| Abstract: | We have observed that dialkylzinc reagents add to atropisomeric 2-formyl arylamides many times faster than they react with other substituted benzaldehyde derivatives. Additionally, with diethylzinc the products were formed with very high diastereoselectivity, affording the syn product (d.r. greater than 95:5), except in one case where epimerization of the product is rapid. In contrast, Grignard and trialkylaluminum reagents afforded the anti diastereomers, with diminished stereoselectivity and formation of reduction products. |
| |
| Keywords: | Dialkylzinc reagents Atropisomeric amides Stereochemistry 1,2-Addition reactions |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
