Chiral bisformamides as effective organocatalysts for the asymmetric one-pot, three-component strecker reaction.
C2-symmetric chiral bisformamides have been shown to catalyze the asymmetric one-pot, three-component Strecker reaction, which produced the alpha-amino nitriles in excellent yields (up to 99%) with good enantioselectivities (up to 86% ee). Optically pure products could be obtained after a single recrystallization. A possible transition state (TS 1) has been proposed to explain the origin of asymmetric inductivity and reactivity according to the geometry of catalyst 2a optimized at the B3LYP/6-31G(d) level and the absolute configuration of product 4a.
Wen
Yuehong
Y
Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Xiong
Yan
Y
Chang
Lu
L
Huang
Jinglun
J
Liu
Xiaohua
X
Feng
Xiaoming
X
D000588:Amines / Q000138:chemical synthesis*; D002384:Catalysis; D005559:Formamides / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis*
D000588:Amines; D005559:Formamides; D009570:Nitriles