Stereoselective Mannich reactions catalyzed by Tröger’s base derivatives in aqueous media
✍ Scribed by Hui Wu; Xiu-mei Chen; Yu Wan; Ling Ye; Hai-qiang Xin; Hua-hong Xu; Cai-hui Yue; Li-ling Pang; Rui Ma; Da-qing Shi
- Book ID
- 104096131
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 164 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A Tröger's base derivative (5,12-dimethyl-3,10-diphenyl-1,3,4,8,10,11-hexaazatetracyclo [6.6.1.0 2,6 .0 9,13 ] pentadeca-2(6),4,9(13),11-tetraenes) was used as an efficient catalyst for the three-component Mannich reactions of aromatic aldehydes and aromatic amines with ketones in water at room temperature. This rapid reaction afforded the corresponding b-amino ketones in good yields with excellent stereoselectivity.
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HBF 4 -catalyzed Mannich-type reaction of silyl enolates with aldimines took place smoothly in aqueous organic solvent to afford b-aminocarbonyl compounds in high yields. The HBF 4 -catalyzed Mannich-type reaction also proceeded smoothly in water without organic solvent in the presence of a surfacta
The catalytic properties of all proteinogenic, acyclic amino acids for direct aldol reaction in H 2 O, assisted by various surfactants, were investigated. The basic and neutral amino acids were shown to be efficient catalysts, giving rise to good-to-excellent yields of adducts (up to 95%), with mode