Scope of the Asymmetric Intramolecular Stetter Reaction Catalyzed by Chiral Nucleophilic Triazolinylidene Carbenes

A highly enantioselective intramolecular Stetter reaction of aromatic and aliphatic aldehydes tethered to different Michael acceptors has been developed. Two triazolium scaffolds have been identified that catalyze the intramolecular Stetter reaction with good reactivity and enantioselectivity. The s...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-03, Vol.73 (6), p.2033-2040
Main Authors: de Alaniz, Javier Read, Kerr, Mark S, Moore, Jennifer L, Rovis, Tomislav
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Alkenes - chemistry
Benzaldehydes - chemistry
Catalysis
Chemical reactivity
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Hydrocarbons - chemistry
Methane - analogs & derivatives
Methane - chemistry
Models, Molecular
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Stereoisomerism
Triazoles - chemistry
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Summary:A highly enantioselective intramolecular Stetter reaction of aromatic and aliphatic aldehydes tethered to different Michael acceptors has been developed. Two triazolium scaffolds have been identified that catalyze the intramolecular Stetter reaction with good reactivity and enantioselectivity. The substrate scope has been examined and found to be broad; both electron-rich and -poor aromatic aldehydes undergo cyclization in high yield and enantioselectivity. The tether can include oxygen, sulfur, nitrogen, and carbon linkers with no detrimental effects. In addition, the incorporation of various tethered Michael acceptors includes amides, esters, thioesters, ketones, aldehydes, and nitriles. The catalyst loading may be reduced to 3 mol % without significantly affecting the reactivity or selectivity of the reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo702313f