A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins.
A new synthesis of 3,3'-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3'-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles with isatins. These tertiary carbinols are formed in high diastereoselectivities, with substitution at various positions of the isatin and the 2-siloxyindole being tolerated.
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
J Michael
JM
Ellis
Larry E
LE
Overman
Huw R
HR
Tanner
Jocelyn
J
Wang
D000447:Aldehydes / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000447:Aldehydes; D007211:Indoles; D007659:Ketones; D017646:Organosilicon Compounds; D007510:Isatin