Asymmetric construction of quaternary carbon stereocenters: high stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes.
[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).
Adhikari
Susanta
S
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
Caille
Sebastien
S
Hanbauer
Martin
M
Ngo
Vinh X
VX
Overman
Larry E
LE
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
D000447:Aldehydes; D026121:Indole Alkaloids; D007211:Indoles; D009942:Organometallic Compounds; D012825:Silicon