Organocatalytic stereoselective mannich reaction of 3-substituted oxindoles.
The asymmetric Mannich reaction of 3-substituted oxindoles and N-Boc imines was investigated for the first time, employing bifunctional thiourea-tertiary amine organocatalysts based on DPEN scaffold. The novel transformations exhibited high diastereoselectivities, and the Mannich adducts bearing adjacent quaternary and tertiary chiral centers were generally obtained in good to excellent enantioselectivities (up to 95% ee).
Tian
Xu
X
Key Laboratory of Drug-Targeting and Drug Deliver System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Jiang
Kun
K
Peng
Jing
J
Du
Wei
W
Chen
Ying-Chun
YC
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000588:Amines; D007097:Imines; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D013890:Thiourea