Enantioselective three-component Kabachnik-Fields reaction catalyzed by chiral scandium(III)-N,N'-dioxide complexes.
The N,N'-dioxide-Sc(III) complex has been applied in the three-component Kabachnik-Fields reaction of aldehydes, 2-aminophenol, and diphenyl phosphite, giving the corresponding alpha-amino phosphonates in good yields with high enantioselectivities (up to 87% ee). The direct Kabachnik-Fields reaction proceeded with extremely high reactivity under mild reaction conditions and could be used for large-scale synthesis of the alpha-amino phosphonates.
Zhou
Xin
X
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Shang
Deju
D
Zhang
Qi
Q
Lin
Lili
L
Liu
Xiaohua
X
Feng
Xiaoming
X
D000447:Aldehydes / Q000737:chemistry*; D000627:Aminophenols / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D010087:Oxides / Q000737:chemistry; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000627:Aminophenols; D063065:Organophosphonates; D010087:Oxides; C027667:2-aminophenol; C507805:diphenyl phosphite; D012538:Scandium