Asymmetric Formal [3+2] Cycloaddition Reaction of Isocyanoesters to 2‐Oxobutenoate Esters by a Multifunctional Chiral Silver Catalyst

Song, Jin; Guo, Chang; Chen, Peng‐Hao; Yu, Jie; Luo, Sanzhong; Gong, Liu‐Zhu

doi:10.1002/chem.201100636

Cited by 95 publications

(42 citation statements)

References 51 publications

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“…Herein we report a highly enantioselective (up to 99% ee) 15 Michael addition of un-substituted α-isocyanoester 2 to 3-methyl-4-nitro-5-styrylisoxazoles 1a-m (Scheme 1) that run under phase transfer catalysis. This reaction provided exclusively mono alkylated compounds 3a-m, whose synthetic relevance was demonstrated by their conversion to 2,3-dihydropyrroles 4a-m 20 and pyrrolidines 7-9.…”

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confidence: 99%

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Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions

et al. 2015

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confidence: 99%

“…2, 60 Scheme 2). 15 Xu and Wang developed a diastereoselective and enantioselective Michael addition of 2-substituted isocyanoacetates to N-aryl maleimides catalyzed by bifunctional tertiary amine thioureas (eq. 3, Scheme 2).…”

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Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions

et al. 2015

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“…(38)]. [72] A variety of aromatic substituents is tolerated within the 2-oxobutanoate and the isocyanoacetate.…”

Section: Condensations Leading To Pyrroles and Indolesmentioning

confidence: 99%

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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“…[3+2] cycloadditions of isocyanoesters occur readily, and high enantiocontrol has been realized [119,120].…”

Section: Diverse Dipolar Cycloaddition Reactionsmentioning

confidence: 99%

The Future of Catalysis by Chiral Lewis Acids

Sha

Deng

Doyle

2015

Topics in Organometallic Chemistry

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Even with the rapidly expanding popularity of organocatalysts for organic reactions, chiral metal-based Lewis acid catalysts continue to have a uniquely important role in asymmetric reactions. Their broad applicability to cycloaddition and condensation reactions based on close encountered associations of Lewis base reactants with these chiral Lewis acid catalysts provides architecturally confined complexes that provide high stereocontrol in their chemical reactions.

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Asymmetric Formal [3+2] Cycloaddition Reaction of Isocyanoesters to 2‐Oxobutenoate Esters by a Multifunctional Chiral Silver Catalyst

Cited by 95 publications

References 51 publications

Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions

Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

The Future of Catalysis by Chiral Lewis Acids

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