Organocatalytic Enantioselective Hydroxymethylation of Oxindoles with Paraformaldehyde as C1 Unit
Authors:
- 24 June 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 75 (14) , 4872-4875
Abstract
A bifunctional thiourea−tertiary amine-catalyzed asymmetric hydroxymethylation of 3-substituted oxindoles using paraformaldehyde as the C1 unit was developed. A wide scope of oxindoles, bearing C3 sterically congested quaternary carbon centers, were smoothly obtained in good to excellent yields (up to 99%) and high enantioselectivities (up to 91% ee) under mild reaction conditions. A more significant feature of this approach employs cheap and readily available paraformaldehyde as a hydroxymethylation C1 unit, which is activated by chiral bifunctional thiourea organocatalysts.Keywords
This publication has 80 references indexed in Scilit:
- Evolution of a Synthetic Strategy: Total Synthesis of (±)-Welwitindolinone A IsonitrileJournal of the American Chemical Society, 2008
- Pyrrolidinyl-Spirooxindole Natural Products as Inspirations for the Development of Potential Therapeutic AgentsAngewandte Chemie International Edition, 2007
- Synthesis of 3-substituted-2-oxoindole analogues and their evaluation as kinase inhibitors, anticancer and antiangiogenic agentsEuropean Journal of Medicinal Chemistry, 2006
- Asymmetric Synthesis of Pyrrolidinoindolines. Application for the Practical Total Synthesis of (−)-PhenserineJournal of the American Chemical Society, 2004
- The Asymmetric Intramolecular Heck Reaction in Natural Product Total SynthesisChemical Reviews, 2003
- Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole AlkaloidsEuropean Journal of Organic Chemistry, 2003
- Gelsemine: A Thought‐Provoking Target for Total SynthesisAngewandte Chemie International Edition, 2003
- A Concise Formal Total Synthesis of TMC-95A/B Proteasome InhibitorsOrganic Letters, 2002
- Enantiospecific, Stereospecific Total Synthesis of the Oxindole Alkaloid AlstonisineOrganic Letters, 2002
- Simple indole alkaloids and those with a nonrearranged monoterpenoid unit (1999)Natural Product Reports, 2001