Stereochemical features of the (2 + 2) cycloaddition reactions of chiral allenes. 4. The cycloaddition of enantioenriched 1,3-dimethylallene with methyl propiolate

Pasto, Daniel J.; Sugi, Kiyoaki D.; Alonso, David

doi:10.1021/jo00030a021

Cited by 24 publications

(10 citation statements)

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“…4 , thus slowing racemization of the resulting radical containing carbon. This hypothesis is supported by a report by Pasto, where transfer of chiral information was incomplete in a thermal, intermolecular [2 + 2] cycloaddition reaction between 2,3-pentadiene and methyl propiolate [ 10 ].…”

Section: Resultssupporting

confidence: 59%

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Brummond¹,

Osbourn²

2011

Beilstein J. Org. Chem.

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SummaryA thermal [2 + 2] cycloaddition reaction of allene-ynes has been used to transform chiral non-racemic allenyl oxindoles into chiral non-racemic spirooxindoles containing an alkylidene cyclobutene moiety. The enantiomeric excesses were determined by chiral lanthanide shift NMR analysis and the transfer of chiral information from the allene to the spirooxindole was found to be greater than 95%.

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Section: Resultssupporting

confidence: 59%

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Brummond¹,

Osbourn²

2011

Beilstein J. Org. Chem.

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“…32 The cycloaddition reaction of enantioenriched 1,3-dimethylallene with methyl propiolate was carried out at 130 1C affording two cycloadducts 77 and 78 in a ratio of 41.8 : 58.2, along with some remaining unreacted 1,3-dimethylallene (Scheme 24).…”

Section: Dimerization and Intermolecular [2+2] Cycloadditions Of Allementioning

confidence: 99%

“…Following the series of Pasto's work, the stereochemical features of the [2+2] cycloaddition reaction of 1,3-dimethylallene with methyl propiolate have been reported. 32 The cycloaddition reaction of enantioenriched 1,3-dimethylallene with methyl propiolate was carried out at 130 1C affording two cycloadducts 77 and 78 in a ratio of 41.8 : 58.2, along with some remaining unreacted 1,3-dimethylallene (Scheme 24).…”

Section: Dimerization and Intermolecular [2+2] Cycloadditions Of Alle...mentioning

confidence: 99%

Exploiting [2+2] cycloaddition chemistry: achievements with allenes

2010

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The allene moiety represents an excellent partner for the [2+2] cycloaddition with alkenes and alkynes, affording the cyclobutane and cyclobutene skeletons in a single step. This strategy has been widely studied under thermal, photochemical and microwave induced conditions. More recently, the use of transition metal catalysis has been introduced as an alternative relying on the activation of the allenic component. On the other hand, the intramolecular version has attracted much attention as a strategy for the synthesis of polycyclic compounds in a regio-and stereoselective fashion. This critical review focuses on the most recently developed [2+2] cycloadditions on allenes along with remarkable early works accounting for the mechanism, the regio-and diastereoselectivity of the cycloadducts formed (103 references).

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“…Although stepwise mechanisms have been proposed in some Lewis acid catalyzed [2+2] cycloadditions,2i, 7, 8, 20 the debate between a concerted or a stepwise mechanism for [2+2] cycloaddition is still ongoing 7b. 21 We have not detected any cationic intermediate in this reaction 22. Considering the similar behaviors of allenic esters and allenones in the presence of Lewis acids, we believe that the mechanism proposed for the [2+2] cycloaddition of allenic esters5, 6 could also be used to rationalize the intramolecular [2+2] cycloaddition of ene‐allenones.…”

Section: Methodsmentioning

confidence: 65%

Acid‐Catalyzed Intramolecular [2+2] Cycloaddition of Ene‐allenones: Facile Access to Bicyclo[n.2.0] Frameworks

Zhao¹,

Loh²

2009

Angewandte Chemie

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Stereochemical features of the (2 + 2) cycloaddition reactions of chiral allenes. 4. The cycloaddition of enantioenriched 1,3-dimethylallene with methyl propiolate

Cited by 24 publications

References 0 publications

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles

Exploiting [2+2] cycloaddition chemistry: achievements with allenes

Acid‐Catalyzed Intramolecular [2+2] Cycloaddition of Ene‐allenones: Facile Access to Bicyclo[n.2.0] Frameworks

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