Gold-Catalyzed Direct Activation of Allylic Alcohols in the Stereoselective Synthesis of Functionalized 2-Vinyl-Morpholines

Alcohol versus alcohol: A highly stereocontrolled synthesis of substituted morpholines is realized by means of gold‐catalyzed dehydrative allylic cyclization of diols (see scheme for one example; segphos = 5,5′‐bis[di(3,5‐di‐tert‐butyl‐4‐methyoxyphenyl)phosphine]‐4,4′‐bi‐1,3‐benzodioxole). The prese...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-12, Vol.16 (48), p.14272-14277
Main Authors: Bandini, Marco, Monari, Magda, Romaniello, Alessandro, Tragni, Michele
Format: Article
Language:English
Subjects:
alcohols
asymmetric synthesis
Chemistry
gold catalysis
heterocycles
stereoselectivity
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Summary:Alcohol versus alcohol: A highly stereocontrolled synthesis of substituted morpholines is realized by means of gold‐catalyzed dehydrative allylic cyclization of diols (see scheme for one example; segphos = 5,5′‐bis[di(3,5‐di‐tert‐butyl‐4‐methyoxyphenyl)phosphine]‐4,4′‐bi‐1,3‐benzodioxole). The present methodology represents one of the few examples of enantioselective gold‐catalyzed transformations involving unactivated alkenes.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201002606