Chiral α-Arylethanamines: An Organocatalyst for the Enantioselective α-Amination of Branched Aldehydes

• Published in: European journal of organic chemistry Vol. 2013; no. 14; pp. 2864 - 2868
• Main Authors: Fu, Ji-Ya, Wang, Qi-Lin, Peng, Lin, Gui, Yong-Yuan, Wang, Fan, Tian, Fang, Xu, Xiao-Ying, Wang, Li-Xin
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.05.2013; WILEY‐VCH Verlag; Wiley
• Subjects: Aldehydes; Amination; Amines; Asymmetric catalysis; Chemistry; Chemistry, Organic; Enantioselectivity; Organocatalysis; Physical Sciences; Science & Technology; SYSTEM; KETONES; Amines; Amination; Enantioselectivity; AMINO-ACIDS; CONSTRUCTION; ASYMMETRIC MICHAEL ADDITION; Aldehydes; Asymmetric catalysis; Organocatalysis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201201701

α‐Arylethanamines were investigated as organocatalysts for the α‐amination of branched aldehydes with azodicarboxylates. Optimization identified (R)‐1‐(1‐naphthyl)ethanamine (1g) as an effective and enantioselective organocatalyst; multifunctional chiral quaternary amino aldehydes were successfully obtained in excellent yields (up to 99 %) and with excellent enantioselectivities (up to 98 % ee). α‐Arylethanamine 1g was found to be an effective and enantioselective organocatalyst for the α‐amination of branched aldehydes with azodicarboxylates. Multifunctional chiral quaternary amino aldehydes were successfully obtained in excellent yields (up to 99 %) and with excellent enantioselectivities (up to 98 % ee).