Asymmetric Construction of Quaternary Carbon Stereocenters:  High Stereoselection in Mukaiyama Aldol Reactions of 2-Siloxyindoles with Chiral Aldehydes

• Published in: Organic letters Vol. 7; no. 13; pp. 2795 - 2797
• Main Authors: Adhikari, Susanta, Caille, Sebastien, Hanbauer, Martin, Ngo, Vinh X, Overman, Larry E
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 23.06.2005; Amer Chemical Soc
• Subjects: Aldehydes - chemistry; Chemistry; Chemistry, Organic; Indole Alkaloids - chemical synthesis; Indole Alkaloids - chemistry; Indoles - chemical synthesis; Indoles - chemistry; Molecular Structure; Organometallic Compounds - chemical synthesis; Organometallic Compounds - chemistry; Physical Sciences; Science & Technology; Silicon - chemistry; Stereoisomerism; ENANTIOSELECTIVE CONSTRUCTION; METABOLITES
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol051172+

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 α carbon is described. When the C3 substituent of the prochiral nucleophile is aryl or heteroaryl, stereoselectivity is high (10−80:1).