Palladium-catalyzed enantioselective oxidation of chiral secondary alcohols: access to both enantiomeric series.
نویسندگان
چکیده
Palladium-Catalyzed Enantioselective Oxidation of Chiral Secondary Alcohols: Access to Both Enantiomeric Series David C. Ebner, Raissa M. Trend, Cédric Genet, Matthew J. McGrath, Peter O’Brien*, and Brian M. Stoltz* The Arnold and Mabel Beckman Laboratories of Chemical Synthesis Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena, California 91125 (USA) Department of Chemistry University of York Heslington, York, YO10 5DD (UK)
منابع مشابه
Improved Catalyst Design for the Palladium-Catalyzed Enantioselective Oxidation of Chiral Secondary Alcohols: Access to Both Enantiomeric Series
Enantioenriched alcohols are ubiquitous in the structures and syntheses of natural products and pharmaceuticals. Catalytic, asymmetric alcohol oxidation can be a useful method to access these molecules.[1] Previously, we reported the development of an aerobic kinetic resolution of alcohols by catalytic [Pd(nbd)Cl2] (1, nbd = norbornadiene) and the naturally occurring alkaloid (−)-sparteine (sp,...
متن کاملThe palladium-catalyzed aerobic kinetic resolution of secondary alcohols: reaction development, scope, and applications.
The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbona...
متن کاملPalladium-catalyzed enantioselective oxidation of alcohols: a dramatic rate acceleration by Cs2CO3/t-BuOH.
[reaction: see text] The addition of Cs(2)CO(3) and t-BuOH provides a dramatic rate acceleration in the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols while maintaining the selectivity of the process.
متن کاملEnantioselective oxidation of racemic secondary alcohols catalyzed by chiral Mn(III)-salen complexes with N-bromosuccinimide as a powerful oxidant.
We demonstrate an efficient enantioselective oxidation of secondary alcohols catalyzed by Mn(III)-salen complex using N-bromosuccinimide (NBS) as the oxidant. The new protocol is very efficient for the oxidative kinetic resolution of a variety of secondary alcohols, including ortho-substituted benzylic alcohols.
متن کاملPalladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization–Borylation of Enallenes**
An enantioselective oxidative carbocyclization-borylation of enallenes that is catalyzed by palladium(II) and a Brønsted acid was developed. Biphenol-type chiral phosphoric acids were superior co-catalysts for inducing the enantioselective cyclization. A number of chiral borylated carbocycles were synthesized in high enantiomeric excess.
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عنوان ژورنال:
- Angewandte Chemie
دوره 47 34 شماره
صفحات -
تاریخ انتشار 2008