Highly Regio-, Diastereo-, and Enantioselective Mannich Reaction of Allylic Ketones and Cyclic Ketimines: Access to Chiral Benzosultam.
An organocatalytic asymmetric Mannich reaction of allylic ketones with cyclic N-sulfonyl α-iminoester has been developed. By using a saccharide-derived chiral tertiary amino-thiourea catalyst, a range of allylic ketones and N-sulfonyl ketimines reacted smoothly to afford tetrasubstituted α-amino esters in high yields with good to excellent regio-, diastero-, and enantioselectivities.
Department of Chemistry, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, P. R. of China.
Baokun
B
Qiao
Department of Chemistry, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, P. R. of China.
Yin-Jun
YJ
Huang
Department of Chemistry, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, P. R. of China.
Jing
J
Nie
Department of Chemistry, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, P. R. of China.|State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, P. R. of China.
Jun-An
JA
Ma
D002384:Catalysis; D004952:Esters; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry
D004952:Esters; D007097:Imines; D007659:Ketones; D009570:Nitriles; D013449:Sulfonamides; C542835:ketimine; D013890:Thiourea