Threonine-surfactant organocatalysts for the highly diastereo- and enantioselective direct anti-Mannich reactions of hydroxyacetone

✍ Scribed by Chuanlong Wu; Xiangkai Fu; Xuebing Ma; Shi Li; Chao Li

• Book ID: 104098256
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 286 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.08.085

✦ Synopsis

In this work, several new L-threonine derivatives as organocatalysts were synthesized in one step for the first time by the reaction of threonine with acyl chlorides at room temperature in trifluoroacetic acid on a large-scale without protecting groups involved or chromatographic techniques, and those threonine-surfactant organocatalysts mediated the direct asymmetric anti-Mannich reactions of hydroxyacetone and anilines with aldehydes to synthesize anti-1,2-amino alcohols in good yields (75-93%) and highly enantioselectivities (up to 99% ee).