title: Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates.
abstract: A cascade aldol-cyclization reaction between 3-isothiocyanato oxindoles and α-ketophosphonates has been developed for the synthesis of β-amino-α-hydroxyphosphonate derivatives. Catalyzed by a quinine-based tertiary amino-thiourea derivative, this reaction delivers 2-thioxooxazolidinyl phosphonates based on a spirooxindole scaffold bearing two contiguous quaternary stereogenic centers in high yields with excellent diastereo- (up to >20:1 dr) and enantioselectivities (up to >99:1 er).
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science , Bangalore - 560012, India.
authors.forename: Satavisha
authors.initials: S
authors.lastname: Kayal
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science , Bangalore - 560012, India.
authors.forename: Santanu
authors.initials: S
authors.lastname: Mukherjee
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D017879:Isothiocyanates / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D000078183:Oxindoles; D011803:Quinine / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
chemical_list: D000447:Aldehydes; D007211:Indoles; D017879:Isothiocyanates; D063065:Organophosphonates; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; C116609:3-hydroxybutanal; D011803:Quinine; D013890:Thiourea