[4+2] Cycloaddition of Ketenes with <i>N</i>‐Benzoyldiazenes Catalyzed by N‐Heterocyclic Carbenes

Huang, Xueliang; He, Lin; Shao, Pan‐Lin; Song, Ye

doi:10.1002/anie.200804487

Cited by 231 publications

(71 citation statements)

References 36 publications

(10 reference statements)

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“…Very recently, Ye found a carbene-catalyzed asymmetric [4+2] cycloaddition reaction of ketenes with diazenes (Scheme 80) [179]. In the presence of 234a, chi-ral 1,3,4-oxadiazin-6-ones could be generated from the reaction in high yields and enantioselectivity.…”

Section: Nhc (N-heterocyclic Carbene) Catalysismentioning

confidence: 98%

Asymmetric Organocatalysis

Liu

Gong

2011

Asymmetric Catalysis From a Chinese Perspective

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Asymmetric organocatalysis has been receiving considerable attention in the last decade and thereby made tremendous advances. Chinese researchers have also intensified efforts to investigate asymmetric organocatalysis by using diverse types of disciplines, including enamine, iminium, Brønsted acid, carbene, and Lewis base catalysis. As a result, a large number of excellent catalysts and elegant protocols have come out from China. This article summarizes the most representative achievements in enantioselective organocatalysis from Chinese groups.

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Section: Nhc (N-heterocyclic Carbene) Catalysismentioning

confidence: 98%

Asymmetric Organocatalysis

Liu

Gong

2011

Asymmetric Catalysis From a Chinese Perspective

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“…1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 carbene catalyst 55 (Scheme 13). 61 The enantioselectivity was proposed to be a consequence of coplanar 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Deng and coworkers explored a bifunctional cinchona catalyst for a similar transformation. This sequence ultimately led to a formal total synthesis of conagenin.…”

Section: Scheme 4 Kozlowski's Tandem N-alkylation/π-allylationmentioning

confidence: 98%

Recent Advances in Asymmetric Catalytic Methods for the Formation of Acyclic α,α-Disubstituted α-Amino Acids

2014

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Because of their greater stability and unique conformational properties, unnatural amino acids are highly valued by pharmaceutical, biological, and organic chemists. This synopsis surveys the various catalytic methods used to access enantioenriched, acyclic α,α-disubstituted α-amino acids with a focus on the processes developed since 2007, when the last major reviews in this area were published.

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“…A direct evolution of such a system has shortly been developed by the same group toward the enantioselective synthesis of 1,3,4-oxadiazin-6-ones 146, starting from ketenes 143 and suitable Nbenzoyldiazenes 144 (Scheme 18) [50]. A wide screening of various catalysts and reaction conditions highlighted, as strong point of this methodology, the possibility to switch the enantioselectivity by adjusting the substituents in the NHC catalyst.…”

Section: Miscellaneous Cycloaddition Reactionsmentioning

confidence: 98%

An Organocatalytic Approach to the Synthesis of Six-Membered Heterocycles

Gasperi¹,

Punzi²,

Migliorini³

et al. 2011

COC

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"""In the last few years, the new era of organocatalysis opened up an effective and efficient way to high yielding metal free, enantio- and diastereoselective reactions leading to six-membered heterocycles. This review provides an overview of the current achievements in the organocatalytic synthesis of these crucial building blocks. Ranging from hetero-Diels-Alder to cycloadditions, from one step cyclizations to cascade reactions, recent results offer new powerful tools to obtain six membered heterocycles with facile procedures in high yields and stereoselection, often leading to many new stereogenic centres in a single reaction. The total syntheses of natural products having heterocyclic ring formation as crucial stage, are also reported. When available, alternative supported organocatalysts have been examined""

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[4+2] Cycloaddition of Ketenes with N‐Benzoyldiazenes Catalyzed by N‐Heterocyclic Carbenes

Cited by 231 publications

References 36 publications

Asymmetric Organocatalysis

Asymmetric Organocatalysis

Recent Advances in Asymmetric Catalytic Methods for the Formation of Acyclic α,α-Disubstituted α-Amino Acids

An Organocatalytic Approach to the Synthesis of Six-Membered Heterocycles

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