Thiophosphoramide catalyzed asymmetric Michael addition of acetone to functionalized nitrostyrenes: a convenient approach to optically active tetrahydropyrans

Yang, Wu; Lu, Aidang; Liu, Yunfeng; Yu, Xiaolei; Wang, Youming; Wu, Guiping; Song, Haibin; Zhou, Zhenghong; Tang, Chuchi

doi:10.1016/j.tetasy.2010.11.019

Cited by 24 publications

(7 citation statements)

References 65 publications

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“…Similar work was documented by the groups of Wang and Zhou in 2010, who used a bifunctional thiophosphoramide catalyst ( S, aR )‐ 14 to catalyse various hydroxymethyl nitrostyrenes 9 and acetone 13 (Scheme ) . The reaction proceeded smoothly in the presence of triethylamine and nicotinic acid as co‐catalysts to give optically active tetrahydropyrans 15 (46 – 74 % ee ).…”

Section: Mbh Adducts In Organocatalytic Reactionssupporting

confidence: 57%

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 Reactionssupporting

confidence: 57%

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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“…Using thiophosphoramide Cat. 5 as catalyst, an asymmetric [4+2] Michael addition of acetone 109 to functionalized hydroxymethyl nitrostyrenes 106 in order to synthesize the multisubstituted tetrahydropyrans 111 with three stereocenters was reported by Zhou's group in 2010 (Scheme ) . Increasing the amounts of acidic benzoic acid and nicotinic acid produced products within a short reaction time.…”

Section: Asymmetric Catalysis With Chiral Aminementioning

confidence: 99%

Organocatalytic Asymmetric Cascade Reactions Based on Gamma‐Nitro Carbonyl Compound

Guo

Peng

et al. 2018

The Chemical Record

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The significant advancements in asymmetric organocascade reactions have been accomplished during the past decades, paving the way to the efficient and stereoselective construction of structurally complex scaffolds from simple and readily available starting materials. Nitro-containing cyclic compounds have become a privileged molecular library given their broad and promising activities in various therapeutic areas. In various approaches to build these valuable scaffolds, the utility of γ-nitrocarbonyl intermediates is one of the most efficient approaches due to its high efficiency, reliability and versatility. The strategies and catalyst systems described here highlight recent advances in the enantioselective synthesis of nitro-containing cyclic molecules via organocascade strategies based on γ-nitrocarbonyl intermediates. Various organocatalysts with distinct activation modes have found application in providing these sophisticated compounds. This review is organized according to the types of organocatalyst. These methods are of importance for the construction of complex chiral cyclic frameworks and the design of new pharmaceutical compounds. We believe that compounds based on nitro-containing cyclic skeletons have the potential to provide novel therapeutic agents and useful biological tools.

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“…In 2010, Zhou and co-workers attempted the nitro-Michael addition of acetone, which is known as a problematic substrate for this reaction, to MBH alcohol 10 in the presence of thiophosphoramide (S,aR)-74 (Scheme 18). 46 This reaction leads to the formation of single diastereomers of tetrahydropyrans 73 in moderate to good yields and in moderate enantioselectivities. .…”

Section: Primary Mbh Alcohols In Asymmetric Reactionsmentioning

confidence: 99%

α-Functionalization of Nitroalkenes and Its Applications in Organic Synthesis

Nair

Kumar

Namboothiri

2016

Synlett

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The applications of Morita-Baylis-Hillman (MBH) and Rauhut-Currier (RC) adducts of nitroalkenes in the synthesis of various carbo-and heterocycles are summarized in this review. In recent years, the MBH adducts and their derivatives such as acetates and bromides have served as efficient synthons for the synthesis of bioactive compounds including natural products. The close proximity of various functional groups makes the MBH and RC adducts extremely valuable substrates in multicomponent and cascade reactions, including annulations, organocatalysis, and kinetic resolution, to name a few.

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Thiophosphoramide catalyzed asymmetric Michael addition of acetone to functionalized nitrostyrenes: a convenient approach to optically active tetrahydropyrans

Cited by 24 publications

References 65 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

Organocatalytic Asymmetric Cascade Reactions Based on Gamma‐Nitro Carbonyl Compound

α-Functionalization of Nitroalkenes and Its Applications in Organic Synthesis

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