(Chemical Equation Presented) Addition of Grignard reagents to chiral imines derived from isatine afforded chiral, optically enriched 3-substituted 3-aminooxindoles in satisfactory yields and diastereoisomeric ratios. A general protocol is described for the addition of alkyl, alkenyl, and aryl Grignard reagents. In one case, the absolute configuration at C3 was determined and the selective N-deprotection was described, enabling further synthetic transformations of the reaction product.
Grignard Addition to Imines Derived from Isatine: A Method for the Asymmetric Synthesis of Quaternary 3-Aminooxindoles / G. Lesma, N. Landoni, T. Pilati, A. Sacchetti, A. Silvani. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 74:12(2009), pp. 4537-4541. [10.1021/jo900623c]
Grignard Addition to Imines Derived from Isatine: A Method for the Asymmetric Synthesis of Quaternary 3-Aminooxindoles
G. LesmaPrimo
;N. LandoniSecondo
;A. SilvaniUltimo
2009
Abstract
(Chemical Equation Presented) Addition of Grignard reagents to chiral imines derived from isatine afforded chiral, optically enriched 3-substituted 3-aminooxindoles in satisfactory yields and diastereoisomeric ratios. A general protocol is described for the addition of alkyl, alkenyl, and aryl Grignard reagents. In one case, the absolute configuration at C3 was determined and the selective N-deprotection was described, enabling further synthetic transformations of the reaction product.
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