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.
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Bandini et al. (2010) studied this question.
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