Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives:  Enantioselective Synthesis of β-Aryl-β-Amino Acids

• Published in: Journal of the American Chemical Society Vol. 124; no. 44; pp. 12964 - 12965
• Main Authors: Wenzel, Anna G, Jacobsen, Eric N
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 06-11-2002
• Subjects: Acetals - chemistry; Amino Acids - chemical synthesis; Catalysis; Chemistry; Exact sciences and technology; Formic Acid Esters - chemistry; Organic chemistry; Stereoisomerism; Thiourea - analogs & derivatives; Thiourea - chemistry; Acetal; Catalytic reaction; Enantioselectivity; Aminoacid; Homogeneous catalysis; Mannich reaction; Asymmetric reaction; Experimental study; Aldimine
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja028353g

Highly enantioselective addition reactions between silyl ketene acetals and N-Boc aldimines are catalyzed by the thiourea-based catalyst 1c. Extraordinary scope is observed in this methodology with regard to the imine substrate, with aryl and heteroaromatic derivatives generally affording nearly quantitative yields of β-amino ester product in up to 98% enantioselectivity.