Organocatalytic and highly stereoselective direct vinylogous Mannich reaction.
The first direct asymmetric vinylogous Mannich (AVM) reaction of alpha,alpha-dicyanoolefins and N-Boc aldimines was described promoted by a simple chiral bifunctional thiourea-tertairy amine organocatalyst. The reaction was highly efficient (S/C up to 1000) and regio-, stereoselective (generally >99% de, 96 to >99.5% ee) at room temperature for a broad array of substrates. Enantiomerically pure delta-amino acid could be smoothly prepared from the adduct.
Liu
Tian-Yu
TY
Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Cui
Hai-Lei
HL
Long
Jun
J
Li
Bang-Jing
BJ
Wu
Yong
Y
Ding
Li-Sheng
LS
Chen
Ying-Chun
YC
D000588:Amines / Q000138:chemical synthesis*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
D000588:Amines; D000596:Amino Acids; D009570:Nitriles; D014753:Vinyl Compounds; D013890:Thiourea