Enantioselective [4 + 2] Cycloadditions of o-Quinone Methides:  Total Synthesis of (+)-Mimosifoliol and Formal Synthesis of (+)-Tolterodine

The first example of an enantioselective cycloaddition of an o-quinone methide (o-QM) with a chiral enol ether is described along with the total synthesis of (+)-mimosifoliol and the formal synthesis of (+)-tolterodine. These syntheses exemplify a three-component, one-pot benzopyran approach for the...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-12, Vol.69 (26), p.9196-9203
Main Authors: Selenski, Carolyn, Pettus, Thomas R. R
Format: Article
Language:English
Subjects:
Acrylates - chemical synthesis
Benzhydryl Compounds - chemical synthesis
Chemistry
Cresols - chemical synthesis
Crystallography, X-Ray
Exact sciences and technology
Guaiacol - analogs & derivatives
Guaiacol - chemical synthesis
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Indolequinones - chemistry
Models, Molecular
Noncondensed benzenic compounds
Organic chemistry
Phenylpropanolamine - chemical synthesis
Preparations and properties
Spectrum Analysis
Stereoisomerism
Tolterodine Tartrate
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Summary:The first example of an enantioselective cycloaddition of an o-quinone methide (o-QM) with a chiral enol ether is described along with the total synthesis of (+)-mimosifoliol and the formal synthesis of (+)-tolterodine. These syntheses exemplify a three-component, one-pot benzopyran approach for the construction of chiral benzylic junctions. Cycloadditions of various enol ethers and o-QMs are examined, and diastereoselectivities >95% are obtained with trans-2-phenyl-1-cyclohexanol and 2,2-diphenylcyclopentanol vinyl ethers.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048703c