Camphor-derived C1-symmetric chiral diamine organocatalysts for asymmetric Michael addition of nitroalkanes to enones.
A series of stable C(1)-symmetric chiral diamines (2a–2l) were conveniently synthesized by condensing exo-(-)-bornylamine or (+)-(1S,2S,5R)-menthylamine with various commercially available Cbz-protected amino acids. Among them, 2a can efficiently promote the Michael addition of nitroalkanes to a broad scope of enones with high yields (up to 96%) and excellent enantioselectivities (up to 98%) under mild conditions.
School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, People's Republic of China.
Yirong
Y
Zhou
Qiang
Q
Liu
Yuefa
Y
Gong
D000473:Alkanes / Q000737:chemistry*; D002384:Catalysis; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*
D000473:Alkanes; D003959:Diamines; D007659:Ketones; D009574:Nitro Compounds