Organocatalytic Kinetic Resolution of Racemic Secondary Nitroallylic Alcohols Combined with Simultaneous Desymmetrization of Prochiral Cyclic Anhydrides

Roy, Suparna; Chen, Kan Fu; Gurubrahamam, Ramani; Chen, Kwunmin

doi:10.1021/jo501882q

Cited by 21 publications

(13 citation statements)

References 44 publications

(17 reference statements)

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“…A reaction based on a similar concept was performed by Chen et al. for the reaction of a secondary nitroallylic alcohol 7 and prochiral cyclic anhydrides 35 in the presence of a cinchonidine‐derived thiourea bifunctional catalyst 33 . The chemical transformation proceeded efficiently to give hemiesters with up to 99 % ee .…”

Section: Mbh Adducts In Organocatalytic Reactionsmentioning

confidence: 97%

Morita–Baylis–Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis

Huang

Anwar

Chen

2016

The Chemical Record

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The Morita-Baylis-Hillman (MBH) reaction is one of the most useful and efficient protocols for constructing new carbon-carbon bonds between an activated olefin and electrophiles in the presence of a tertiary amine/phosphine. Herein, we present the use of MBH alcohols, which are obtained from the reaction of nitrostyrenes with aldehydes, as well as acetates and amines derived thereof in several organocatalytic transformations. Densely functionalised MBH adducts can also be used to synthesise substituted heteroaromatic compounds, such as furan, pyrrole, pyrazole and imidazole derivatives.

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Section: Mbh Adducts In Organocatalytic Reactionsmentioning

confidence: 97%

Morita–Baylis–Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis

Huang

Anwar

Chen

2016

The Chemical Record

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“…Chen et al. recently reported the OCKR of racemic secondary nitroallylic alcohols 28 , which was achieved simultaneously with the desymmetrization of prochiral cyclic anhydrides 88 under cinchonidine‐derived thiourea 92 catalysis . The chemical yields obtained for hemiesters 93 were good with high diastereo‐ and enantioselectivities (up to >20:1 dr and 99 % ee ), and enantioenriched ( S )‐ 28 (up to 95 % ee ) was also recovered (Scheme ).…”

Section: Organocatalytic Kr By Synergistic Association With Desymmetmentioning

confidence: 99%

Recent Advances in Organocatalytic Kinetic Resolution for the Synthesis of Functionalized Products

et al. 2015

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This Minireview describes organocatalytic kinetic resolution (OCKR) that has evolved on the basis of using small organic catalysts through enamine/iminium ion, N‐heterocyclic carbene, and hydrogen‐bonding catalysis. The review includes the use of recent methodologies for which the evolution of OCKR mainly involves creating new stereogenic center(s) in functionalized products through the formation of a C−C, C−N, C−O, C−X, or C−S bond. The combination of OCKR with sequential reactions and its association with desymmetrization and dynamic kinetic resolution are also described.

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“…36 Each enantiomer of the racemic secondary nitroallylic alcohol, (AE)-ethyl 2-hydroxy-3-nitro-4-phenylbut-3-(E)-enoate, could be kinetically resolved by reacting with 3-substituted glutaric anhydrides using cinchonidine-derived thiourea catalyst C-15 (Scheme 11). 36 Each enantiomer of the racemic secondary nitroallylic alcohol, (AE)-ethyl 2-hydroxy-3-nitro-4-phenylbut-3-(E)-enoate, could be kinetically resolved by reacting with 3-substituted glutaric anhydrides using cinchonidine-derived thiourea catalyst C-15 (Scheme 11).…”

Section: S W Richardsonmentioning

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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Organocatalytic Kinetic Resolution of Racemic Secondary Nitroallylic Alcohols Combined with Simultaneous Desymmetrization of Prochiral Cyclic Anhydrides

Cited by 21 publications

References 44 publications

Morita–Baylis–Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis

Morita–Baylis–Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis

Recent Advances in Organocatalytic Kinetic Resolution for the Synthesis of Functionalized Products

Organocatalytic enantioselective desymmetrisation

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