A general organic catalyst for asymmetric addition of stabilized nucleophiles to acyl imines |
| |
Authors: | Christiane M Bode |
| |
Institution: | Department of Chemistry and Center for Chemical Methodology and Library Development, Life Science and Engineering Building, Boston University, 24 Cummington Street, Boston, MA 02215, USA |
| |
Abstract: | Cinchona alkaloid-derived thiourea catalysts promote nucleophilic additions to acyl imines for the asymmetric synthesis of secondary amine adducts. The hydroquinine-derived thiourea catalyst efficiently promotes the aza-Henry reaction of nitroalkane with acyl imines, affording β-nitroamines in good yields with enantioselectivities of 90-98% ee and diastereoselectivities up to 97%. The scope of the reaction also includes dimethyl malonate as a nucleophile to access β-amino esters in high enantiopurity. Under the optimized reaction conditions, secondary amine adducts of high enantiopurity are generated based on various aromatic and α,β-unsaturated acyl imines. |
| |
Keywords: | Cinchona alkaloids Thiourea Organic catalysis Imines Mannich reaction Aza-Henry reaction |
本文献已被 ScienceDirect 等数据库收录! |
|