A Multicatalyst System for the One‐Pot Desymmetrization/Oxidation of <i>meso</i>‐1,2‐Alkane Diols

Müller, Christian; Hrdina, Radim; Wende, Raffael C.; Schreiner, Peter R.

doi:10.1002/chem.201100498

Cited by 35 publications

(29 citation statements)

References 52 publications

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“…Indeed, by replacing the C-terminal methyl ester group of peptide 273 with a TEMPO-amide functionality they obtained the first member of organic multicatalysts 278 (Boc-L-Pmh-A Gly-L-Cha-L-Phe-NH-TEMPO), bearing two orthogonal catalytic moieties (Scheme 42). 13,112 Remarkably, this proof-of-principle study revealed that the multicatalyst 278 shows an increased oxidation activity compared to TEMPO itself. As a result, the amounts of m-CPBA (3.0 instead of up to 8.0 equivalents) and tetrabutylammonium bromide (5 mol% instead of 30 mol%) could be significantly reduced.…”

Section: Multicatalyst Approachesmentioning

confidence: 77%

Evolution of asymmetric organocatalysis: multi- and retrocatalysis

2012

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The evolution of organocatalysis led to various valuable approaches, such as multicomponent as well as domino and tandem reactions. Recently, organomulticatalysis, i.e., the modular combination of distinct organocatalysts enabling consecutive reactions to be performed in one pot, has become a powerful tool in organic synthesis. It allows the construction of complex molecules from simple and readily available starting materials, thereby maximizing reaction efficiency and sustainability. A logical extension of conventional multicatalysis is a multicatalyst, i.e., a catalyst backbone equipped with independent, orthogonally reactive catalytic moieties. Herein we highlight the impressive advantages of asymmetric organomulticatalysis, examine its development, and present detailed reactions based on the catalyst classes employed, ranging from the very beginnings to the latest multicatalyst systems. R. C. Wende was born inRosenberg (Olesno), Poland, in 1984. He studied chemistry at the Justus-Liebig University, Giessen, where he obtained his B. Sc. degree in 2008 and his M. Sc. degree in 2010. Currently he is working on his PhD under the supervision of P. R. Schreiner. His research focuses on the development of novel synthetic oligopeptide and thiourea organocatalysts for multicatalysis reactions.

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Section: Multicatalyst Approachesmentioning

confidence: 77%

Evolution of asymmetric organocatalysis: multi- and retrocatalysis

2012

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“…7). 103 Additionally, the rate of oxidation was increased using oligopeptide catalyst C-63 compared to the use of free TEMPO. This led to the design of several oligopeptide catalysts containing independent catalyst moieties for both desymmetrisation and oxidation.…”

Section: Acylation Of Diolsmentioning

confidence: 99%

Organocatalytic enantioselective desymmetrisation

et al. 2016

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Organocatalytic enantioselective desymmetrisation of achiral or meso compounds is a powerful strategy for the construction of enantiomerically enriched complex molecules, often with multiple stereocentres and in high selectivities. Recent years have seen increasing use of organocatalysts in desymmetrisation methodology, in contrast to traditional metal- or enzyme-catalysed reactions, with many impressive advances made in the current decade. This review will provide an overview of the field since 2010, with the aim of highlighting both the practical applications and elegance of enantioselective desymmetrisation to the wider synthetic community.

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“…The multicatalyst system OC‐21 has been designed to perform one pot desymmetrization/oxidation of meso ‐diols 33. With this catalyst oxidation step occurred under milder conditions than in the separate protocols.…”

Section: Histidine‐based Peptidesmentioning

confidence: 99%

“…[32] The multicatalyst system OC-21 has been designed to perform one pot desymmetrization/oxidation of meso-diols. [33] With this catalyst oxidation step occurred under milder conditions than in the separate protocols. Under optimized reaction conditions yields and selectivities in desymmetrization of several meso-diols are generally good (Scheme 21).…”

Section: Histidine-based Peptidesmentioning

confidence: 99%

Organocatalyzed Enantioselective Desymmetrization of Diols in the Preparation of Chiral Building Blocks

Dı́az-de-Villegas

Gálvez

Badorrey

et al. 2012

Chemistry A European J

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Desymmetrization of diols is a powerful tool to the synthesis of chiral building blocks. Among the different approaches to perform discrimination between both enantiotopic hydroxyl groups, the organocatalytic approach has gained importance in the last years. A diverse range of organocatalysts has been used to efficiently promote this enantioselective transformation and this Minireview examines the different contributions in this field.

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A Multicatalyst System for the One‐Pot Desymmetrization/Oxidation of meso‐1,2‐Alkane Diols

Cited by 35 publications

References 52 publications

Evolution of asymmetric organocatalysis: multi- and retrocatalysis

Evolution of asymmetric organocatalysis: multi- and retrocatalysis

Organocatalytic enantioselective desymmetrisation

Organocatalyzed Enantioselective Desymmetrization of Diols in the Preparation of Chiral Building Blocks

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