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- Title
Diastereoselective Construction of 3-Aminooxindoles with Adjacent Stereocenters: Stereocontrolled Addition of γ-Substituted Allylindiums to Isatin Ketimines.
- Authors
Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Rani, Soniya; Mahajan, Shivam; Solanki, Jagmohan; Yasuda, Makoto; Baba, Akio
- Abstract
The diastereoselective construction of 3-allyl-3-aminooxindoles that have two adjacent stereocenters has been achieved by the In-promoted Barbier-type addition of γ-substituted allylic halides to the C=N bond of isatin ketimines. The reactions of cinnamyl-, crotyl-, and geranylindium compounds with isatin ketimines proceeded in either aqueous or alcohol solution. The addition of a cyclohexenylindium species to an isatin ketimine was carried out in N,N-dimethylformamide (DMF), and the addition of ethyl 4-bromocrotonate to an isatin ketimine in EtOH gave oxindole-based β-amino acid scaffolds. In all of these processes, the reaction conditions were screened to obtain the respective 3-allyl-3-aminooxindoles with very high stereoselectivity. In addition, plausible TS models are proposed, and representative synthetic transformations were carried out by using the oxindole-based β- amino acid scaffolds. Furthermore, the stereochemistry of representative compounds were unequivocally established by single-crystal X-ray structure analysis.
- Subjects
STEREOSELECTIVE reactions; IMINE synthesis; ORGANIC synthesis; SINGLE crystals spectra; OXINDOLES
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 19, p4168
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500340