Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes.
A chiral Lewis acid catalyst was prepared by mixing 2 equiv of chiral binol-derived organophosphoric acid and 1 equiv of Et(2)AlCl. In the presence of a catalytic amount of [4j](2)Al(III)Cl complex (0.05 equiv), reaction between alpha-isocyanoacetamides (2) and aldehydes (3) afforded the corresponding 5-aminooxazoles (1) in good yields and enantioselectivities. Complex [4j](2)Al(III)Cl isolated as a white solid displayed similar reactivity as that prepared in situ.
Yue
Tao
T
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Wang
Mei-Xiang
MX
Wang
De-Xian
DX
Masson
Géraldine
G
Zhu
Jieping
J
D000447:Aldehydes / Q000737:chemistry*; D000535:Aluminum / Q000737:chemistry*; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010755:Organophosphates / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D000447:Aldehydes; D003486:Cyanides; D010755:Organophosphates; D000535:Aluminum