The oxidation of 4-(1-cyclohexen-1-yl)-morpholine with lead tetraacetate

Corbani, F.; Rindone, Bruno; Scolastico, Carlo

doi:10.1016/s0040-4039(01)84884-x

“…在 1969 年, 氨基苯并三唑首次被 Campbell 和 Rees 在氧化剂作用下产生苯炔中间体 [9] . 随后 Pb(OAc) 4 作为氧化剂被广泛使用 [10] , 为发展更高效、绿色的有机合成方法, 作者通过电化学阳极氧化的方法首次成功实现了高活性苯炔中间体的生成, 但如何使催化活化的烯胺中间体更好地捕获苯炔中间体, 仍然是不对称催化反应的难点. 作者发现 Co(OAc)…”

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Catalytic Asymmetric Electrochemical α-Arylation of Cyclic β-Ketocarbonyls with Anodic Benzyne Intermediates

Guo¹

2020

Chin. J. Org. Chem.

1

0

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Catalytic Asymmetric Electrochemical α‐Arylation of Cyclic β‐Ketocarbonyls with Anodic Benzyne Intermediates

Li

¹

,

Li

²

,

Fu

³

et al. 2020

View full text Add to dashboard Cite

Asymmetric catalysis with benzyne remains elusive because of the highly fleeting and nonpolar nature of benzyne intermediates. Reported herein is an electrochemical approach for the oxidative generation of benzynes (cyclohexyne) and its successful merging with chiral primary aminocatalysis, formulating the first catalytic asymmetric enamine–benzyne (cyclohexyne) coupling reaction. Cobalt acetate was identified to stabilize the in situ generated arynes and facilitate its coupling with an enamine. This catalytic enamine‐benzyne protocol provides a concise method for the construction of diverse α‐aryl (α‐cyclohexenyl) quaternary carbon stereogenic centers with good stereoselectivities.

show abstract

Catalytic Asymmetric Electrochemical α‐Arylation of Cyclic β‐Ketocarbonyls with Anodic Benzyne Intermediates

Li

¹

,

Li

²

,

Fu

³

et al. 2020

View full text Add to dashboard Cite

Asymmetric catalysis with benzyne remains elusive because of the highly fleeting and nonpolar nature of benzyne intermediates. Reported herein is an electrochemical approach for the oxidative generation of benzynes (cyclohexyne) and its successful merging with chiral primary aminocatalysis, formulating the first catalytic asymmetric enamine–benzyne (cyclohexyne) coupling reaction. Cobalt acetate was identified to stabilize the in situ generated arynes and facilitate its coupling with an enamine. This catalytic enamine‐benzyne protocol provides a concise method for the construction of diverse α‐aryl (α‐cyclohexenyl) quaternary carbon stereogenic centers with good stereoselectivities.

show abstract

The oxidation of 4-(1-cyclohexen-1-yl)-morpholine with lead tetraacetate

Cited by 9 publications

References 4 publications

Catalytic Asymmetric Electrochemical α-Arylation of Cyclic β-Ketocarbonyls with Anodic Benzyne Intermediates

Catalytic Asymmetric Electrochemical α-Arylation of Cyclic β-Ketocarbonyls with Anodic Benzyne Intermediates

Catalytic Asymmetric Electrochemical α‐Arylation of Cyclic β‐Ketocarbonyls with Anodic Benzyne Intermediates

Catalytic Asymmetric Electrochemical α‐Arylation of Cyclic β‐Ketocarbonyls with Anodic Benzyne Intermediates

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