Catalytic Additions of Acylsilanes to Imines: An Acyl Anion Strategy for the Direct Synthesis of α-Amino Ketones
- 9 October 2004
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (23) , 4363-4366
- https://doi.org/10.1021/ol0481129
Abstract
The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected alpha-amino ketones in the correct oxidation state.Keywords
This publication has 17 references indexed in Scilit:
- Nucleophilic Carbenes in Asymmetric OrganocatalysisAccounts of Chemical Research, 2004
- Catalyzed Reactions of Acyl Anion EquivalentsAngewandte Chemie International Edition in English, 2004
- The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and KetonesJournal of the American Chemical Society, 2004
- Diastereoselective reduction of α-aminoketones: Synthesis of anti- and syn-β-aminoalcoholsCanadian Journal of Chemistry, 2004
- Functionalized amido ketones: new anticonvulsant agentsBioorganic & Medicinal Chemistry, 2003
- Facile Approach to Enantiomerically Pure α-Amino Ketones by Friedel−Crafts Aminoacylation and Their Conversion into Peptidyl KetonesThe Journal of Organic Chemistry, 2001
- Synthesis of Allylic and Propargylic Primary Amines by Reaction of Organometallic Reagents with α-Amidoalkyl SulfonesThe Journal of Organic Chemistry, 1999
- Kinetics of C(2α)-Proton Abstraction from 2-Benzylthiazolium Salts Leading to Enamines Relevant to Catalysis by Thiamin-Dependent EnzymesJournal of the American Chemical Society, 1997
- A regiospecific synthesis of 1,4-disubstituted imidazolesThe Journal of Organic Chemistry, 1994
- Molecular rearrangements of organosilicon compoundsAccounts of Chemical Research, 1974