Bifunctional thiourea-promoted cascade aza-Michael-Henry-dehydration reactions: asymmetric preparation of 3-nitro-1,2-dihydroquinolines.
A cascade aza-Michael-Henry-dehydration reaction catalyzed by quinidine-derived tertiary amine-thiourea catalyst was developed via installation of suitable electron withdrawing groups at the amino function of aniline. This strategy led to a one-step preparation of chiral 3-nitro-1,2-dihydroquinolines in high yields and with up to 90% enantiomeric excesses.
Liu
Xiaoqian
X
Department of Chemistry and Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, Singapore, Republic of Singapore.
Lu
Yixin
Y
D000588:Amines / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003681:Dehydration; D015394:Molecular Structure; D009600:Nitroquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D011802:Quinidine / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000588:Amines; D001391:Azo Compounds; D009600:Nitroquinolines; D013890:Thiourea; D011802:Quinidine