title: Asymmetric construction of quaternary carbon stereocenters: high stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes.
abstract: [reaction: see text] A new synthesis of enantiopure 3,3-disubstituted oxindoles by stereoselective Mukaiyama aldol reaction of 3-substituted 2-siloxyindoles and chiral, enantiopure aldehydes having nitrogen or oxygen substituents at the alpha carbon is described. When the C3 substituent of the prochiral nucleophile is aryl or heteroaryl, stereoselectivity is high (10-80:1).
authors.affiliation: Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
authors.forename: Susanta
authors.initials: S
authors.lastname: Adhikari
authors.forename: Sebastien
authors.initials: S
authors.lastname: Caille
authors.forename: Martin
authors.initials: M
authors.lastname: Hanbauer
authors.forename: Vinh X
authors.initials: VX
authors.lastname: Ngo
authors.forename: Larry E
authors.initials: LE
authors.lastname: Overman
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D026121:Indole Alkaloids; D007211:Indoles; D009942:Organometallic Compounds; D012825:Silicon