Title
Enantioselective Mannich reaction between rhodanines and isatin-derived ketimines to construct vicinal tetrasubstituted stereocenters
Author
Han Xu, Tian-Chen Kang, Feng Sha, Xin-Yan Wu
Year
2018
Journal
Organic & Biomolecular Chemistry
Abstract
An organocatalytic enantioselective Mannich reaction between rhodanines and isatin-derived ketimines was developed. With 2 mol% of a quinine-based tertiary amine-thiourea catalyst C2, 3,3-disubstituted oxindoles with vicinal tetrasubstituted stereocenters were obtained in moderate-to-excellent yields (43–99%) with excellent diastereoselectivities (98 : 2–99 : 1 dr) and good-to-excellent enantioselectivities (up to 97% ee). The readily available substrates, low catalyst loading and high stereoselectivity are the major features.
Instrument
J-815
Keywords
Circular dichroism, Absolute configuration, Stereochemistry, Organic chemistry