Organocatalytic asymmetric Henry reaction of isatins: Highly enantioselective synthesis of 3-hydroxy-2-oxindoles
- 18 August 2011
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in RSC Advances
- Vol. 1 (3), 389-392
- https://doi.org/10.1039/c1ra00477h
Abstract
Organocatalytic asymmetric Henry reaction of isatins with nitromethane has been achieved with the use of C6′-OH cinchona alkaloid catalyst, affording 3-substituted 3-hydroxy-oxindoles in excellent yields and high enantioselectivities, and this method was successfully applied to the total synthesis of (R)-(+)-dioxibrassinin.Keywords
This publication has 50 references indexed in Scilit:
- Construction of Chiral Quaternary Carbon through Morita–Baylis–Hillman Reaction: An Enantioselective Approach to 3‐Substituted 3‐Hydroxyoxindole DerivativesChemistry – A European Journal, 2010
- Quinidine Thiourea‐Catalyzed Aldol Reaction of Unactivated Ketones: Highly Enantioselective Synthesis of 3‐Alkyl‐3‐hydroxyindolin‐2‐onesAngewandte Chemie-International Edition, 2010
- Enantioselective Synthesis of Spirocyclic Oxindole‐β‐lactones via N‐Heterocyclic Carbene‐Catalyzed Cycloaddition of Ketenes and IsatinsAdvanced Synthesis & Catalysis, 2010
- Asymmetric Addition of Indoles to Isatins Catalysed by Bifunctional Modified Cinchona Alkaloid CatalystsChemistry – A European Journal, 2010
- Facile Creation of 3‐Indolyl‐3‐hydroxy‐2‐oxindoles by an Organocatalytic Enantioselective Friedel–Crafts Reaction of Indoles with IsatinsAdvanced Synthesis & Catalysis, 2010
- Catalytic Asymmetric Synthesis of Substituted 3‐Hydroxy‐2‐OxindolesAngewandte Chemie-International Edition, 2010
- Organocatalytic Enantioselective Cross‐Aldol Reactions of Aldehydes with Isatins: Formation of Two Contiguous Quaternary Centered 3‐Substituted 3‐Hydroxyindol‐2‐onesChemistry – An Asian Journal, 2009
- Enantioselective Allylation, Crotylation, and Reverse Prenylation of Substituted Isatins: Iridium‐Catalyzed C-C Bond‐Forming Transfer HydrogenationAngewandte Chemie-International Edition, 2009
- First Enantioselective Synthesis of (R)‐Convolutamydine B and E with N‐(Heteroarenesulfonyl)prolinamidesChemistry – A European Journal, 2009
- Brassicanal C and two dioxindoles from cabbagePhytochemistry, 1991