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Diastereoselective Construction of 3‐Aminooxindoles with Adjacent Stereocenters: Stereocontrolled Addition of γ‐Substituted Allylindiums to Isatin Ketimines
Author(s) -
Aslam Nayyar Ahmad,
Babu Srinivasarao Arulananda,
Rani Soniya,
Mahajan Shivam,
Solanki Jagmohan,
Yasuda Makoto,
Baba Akio
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500340
Subject(s) - isatin , chemistry , stereocenter , oxindole , stereoselectivity , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
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.