Pd(II)/β-ICD-Cocatalyzed Asymmetric Route to Oxindole Scaffold via Cascade Reaction of Diazoacetamides and MBH-Carbonates

We report an efficient method for asymmetric synthesis of chiral oxindoles. Allyl palladium­(II) chloride dimer (APC)-catalyzed, in combination with β-isocupreidine (β-ICD)-cocatalyzed, reaction of diazoacetamide with Morita–Baylis–Hillman (MBH) carbonates proves to be a facile protocol to access mu...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-09, Vol.81 (18), p.8537-8543
Main Authors: Yang, Yang, Ma, Chaoqun, Thumar, Nilesh J, Hu, Wenhao
Format: Article
Language:English
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Summary:We report an efficient method for asymmetric synthesis of chiral oxindoles. Allyl palladium­(II) chloride dimer (APC)-catalyzed, in combination with β-isocupreidine (β-ICD)-cocatalyzed, reaction of diazoacetamide with Morita–Baylis–Hillman (MBH) carbonates proves to be a facile protocol to access multifunctional oxindoles bearing a C-3 quaternary stereo center. This tandem reaction tolerates a wide variety of functional groups on the both aromatic rings. This method delivers a variety of chiral oxindoles in 50–75% yield and with up to 95:5 dr in most cases along with up to 93:7 er.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01703