Organocatalytic and electrophilic approach to oxindoles with C3-quaternary stereocenters.
A Lewis base-catalyzed asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates derived from isatins has been investigated, which provides an electrophilic pathway to access oxindoles bearing C3-quaternary stereocenters. Excellent diastereoselectivity and high enantioselectivity have been obtained in the vinylogous functionalization of α,α-dicyanoolefin nucleophiles, giving multifunctional products with vicinal quaternary and tertiary chiral carbon centers.
Peng
Jing
J
Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Huang
Xin
X
Cui
Hai-Lei
HL
Chen
Ying-Chun
YC
D000478:Alkylation; D002384:Catalysis; D018360:Crystallography, X-Ray; D004583:Electrons; D007211:Indoles / Q000737:chemistry*; D058115:Lewis Bases / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism
D007211:Indoles; D058115:Lewis Bases; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole