- The Catalytic Asymmetric Intermolecular Prins Reaction
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Despite their significant potential, catalytic asymmetric reactions of olefins with formaldehyde are rare and metal-free approaches have not been previously disclosed. Here we describe an enantioselective intermolecular Prins reaction of styrenes and paraformaldehyde to form 1,3-dioxanes, using confined imino-imidodiphosphate (iIDP) Br?nsted acid catalysts. Isotope labeling experiments and computations suggest a concerted, highly asynchronous addition of an acid-activated formaldehyde oligomer to the olefin. The enantioenriched 1,3-dioxanes can be transformed into the corresponding optically active 1,3-diols, which are valuable synthetic building blocks.
- Diáz-Oviedo, C. David,Maji, Rajat,List, Benjamin
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supporting information
p. 20598 - 20604
(2021/12/14)
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- Palladium-catalyzed regioselective azidation of allylic C-H bonds under atmospheric pressure of dioxygen
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A palladium-catalyzed allylic azidation of alkenes with sodium azide under atmospheric pressure of dioxygen was developed. This methodology provides a new efficient and simple route for accessing allylic azides. Furthermore, the one-pot process consisting of Pd-catalyzed allylic azidation of alkenes and Cu-catalyzed 1,3-dipolar cycloaddition led directly to the 1,2,3-triazole from the alkene. The formed allylic azide can be also in situ reduced to the allylic amine or oxidized to the alkenyl nitrile. the Partner Organisations 2014.
- Chen, Huoji,Yang, Wanfei,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 3340 - 3343
(2014/05/20)
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- Expanding the regioselective enzymatic repertoire: Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta
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The first report of a biocatalytic regioselective oxidative mono-cleavage of dialkenes was successfully achieved employing a cell-free enzyme preparation from Trametes hirsuta at the expense of molecular oxygen. Selected reactions were performed on a preparative scale affording high to excellent conversions and chemoselectivities. The Royal Society of Chemistry 2012.
- Paul, Caroline E.,Rajagopalan, Aashrita,Lavandera, Ivan,Gotor-Fernandez, Vicente,Kroutil, Wolfgang,Gotor, Vicente
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supporting information; experimental part
p. 3303 - 3305
(2012/04/23)
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- A highly effective (Triphenyl phosphite)palladium catalyst for a cross-coupling reaction of allylic alcohols with organoboronic acids
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The cross coupling reaction of aryl and vinyl boronic acids and allylic alcohols proceeded smoothly in toluene or dioxane in the presence of a (triphenyl phosphite)palladium catalyst to give the corresponding allylbenzene derivatives and 1,4-dienes. Neither cocatalysts for promoting C-O bond cleavage of allylic alcohols nor bases for activation of organoboron reagents are required for promoting the coupling process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Kayaki, Yoshihito,Koda, Takashi,Ikariya, Takao
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p. 4989 - 4993
(2007/10/03)
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