Corrigendum: The Benzyne Aza‐Claisen Reaction

Cant, Alastair A.; Bertrand, Guillaume; Henderson, Jaclyn L.; Roberts, Lee R.; Greaney, Michael F.

doi:10.1002/anie.201206624

Cited by 2 publications

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“…Greaney′s group reported an aryne ACR in which the ACR‐induced ring expansion occurred through the addition of a tertiary amine to an electrophilic aryne . The benzyne ACR was successfully extended to the ring expansion of 5‐ and 6‐membered cyclic tertiary amines 19 , thereby providing the corresponding 9‐ and 10‐membered benzannulated cyclic amines 24 , respectively, as shown in Scheme .…”

Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

“…The benzyne ACR was successfully extended to the ring expansion of 5‐ and 6‐membered cyclic tertiary amines 19 , thereby providing the corresponding 9‐ and 10‐membered benzannulated cyclic amines 24 , respectively, as shown in Scheme . The resulting alkene was initially reported to adopt a Z configuration, but was later corrected to be the E configuration …”

Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

“…Previously, it was found that benzyne promoted the ACR‐induced ring expansion of 5‐ and 6‐membered azacycles . Recently, the benzyne‐promoted ACR of 2‐vinylazetidine has also been investigated, as shown in Scheme .…”

Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

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Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

2017

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The aza-Claisen rearrangement,a lso known as the 3-aza-Coper earrangement, has attracted significant attention because it can be used as ac omplimentarym ethodt o access ad iverse range of useful organic molecules. The presence of an itrogen atom at the 3-position enables the tethering of various-sized azacycles, thereby giving ring-expansion strategiest hat take advantage of the aza-Claisen rearrangementadistinct advantage comparedt oo ther [3,3]-sigmatropic rearrangements. Recent advances in aza-Claisen rearrangements have facilitatedo therwise-inaccessible ring expansions in ah ighly stereoselective manner. The utility of aza-Claisen-rearrangement-induced ring-expansion strategies has been exemplified in the synthesis of ad iverse range of naturalp roducts. This Focus Review summarizes recent advancesi na za-Claisen-rearrangement-induced ring-expansion strategy, in particular applicationsi nt he synthesis of bioactive alkaloids.

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Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

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Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

2017

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Tandem Aryne‐Capture/Sigmatropic Rearrangement as a Metal‐Free Entry to Functionalized N‐Aryl Pyrrolidines

Moss

Pocock

Sweeney

2016

Chemistry A European J

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We report a new method for the synthesis of novel N-aryl proline analogues. By reacting an aryne precursor with N-(2-malonyl) tetrahydropyridines in the presence of tetrabutylammonium fluoride (TBAF), a tandem aryne-capture/anion isomerisation/[2,3]-sigmatropic rearrangement is induced, leading to good yields of 3-substituted N-aryl-2-acylpyrrolidines. These products are known subunits of biological probes, sensors and drug-like fragments, and are not easily accessed directly by other methods. The reaction is also notable as the first [2,3]-rearrangement of cyclic ammonium ylides at room temperature.

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Corrigendum: The Benzyne Aza‐Claisen Reaction

Cited by 2 publications

References 0 publications

Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

Tandem Aryne‐Capture/Sigmatropic Rearrangement as a Metal‐Free Entry to Functionalized N‐Aryl Pyrrolidines

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