An Enantioselective Organocatalytic Oxidative Dearomatization Strategy

We have developed a catalytic enantioselective strategy for chemical synthesis wherein flat aromatic molecules are directly converted to complex nonracemic molecular architectures. The process involves oxidative dearomatization of substituted phenols followed by a desymmetrizing secondary amine-cata...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-01, Vol.130 (2), p.404-405
Main Authors: Vo, Ngoc T, Pace, Robert D. M, O'Har, Fionn, Gaunt, Matthew J
Format: Article
Language:English
Subjects:
Catalysis
Hydrocarbons, Aromatic - chemistry
Oxidation-Reduction
Phenols - chemistry
Stereoisomerism
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Summary:We have developed a catalytic enantioselective strategy for chemical synthesis wherein flat aromatic molecules are directly converted to complex nonracemic molecular architectures. The process involves oxidative dearomatization of substituted phenols followed by a desymmetrizing secondary amine-catalyzed asymmetric intramolecular Michael addition and reveals a decalin structure, formed with exquisite control of three new stereogenic centers and an array of exploitable orthogonal functionality, directly from a flat molecule that is devoid of architectural complexity.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja077457u