Selenium Stabilized Carbenium Ions on Organic Synthesis

Silveira, Cláudio C.; Larghi, Enrique L.

doi:10.1590/s0103-50531998000400005

Cited by 7 publications

(3 citation statements)

References 19 publications

(25 reference statements)

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“…Diastereomeric excesses of the soproduced THIQ were not informed. An analogous approach was earlier reported by Silveira and Kaufman 63 during the course of their studies concerning the structure and synthetic applications of carbocations directly linked to an organoselenium group, 64 which exploit the ability of the organoselenium group to stabilize a carbenium ion adjacent to an ester group. …”

Section: Scheme 10mentioning

confidence: 88%

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The intermolecular Pictet-Spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically-active isoquinoline and indole alkaloids

Larghi¹,

Amongero²,

Bracca³

et al. 2005

Arkivoc

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The stereoselective Pictet-Spengler synthesis is one of the currently most important synthetic methodologies for the preparation of polysubstituted optically active tetrahydroisoquinolines and tetrahydro-β-carboline derivatives functionalized on C-1. The intermolecular Pictet-Spengler condensation with chiral carbonyl derivatives constitutes an interesting and useful approach towards this goal, as summarized in this review. Strategies covered, which were developed during the last 15 years, include the intermolecular Pictet-Spengler reaction with the use of carbonyl derivatives tethered to removable chiral auxiliaries and the cyclocondensation of β-arylethylamines with chiral carbonyl components. Brief mention is also made to the occurrence of asymmetric β-carbolines in foodstuffs.

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Section: Scheme 10mentioning

confidence: 88%

“…The suitability of this observation for the elaboration of optically active natural products was successfully tested in several occasions. Along these lines, Czarnocki and coworkers disclosed a total synthesis of (-)-carnegine (27) which employs R-(+)-glyceraldehyde (64) and dopamine (42) …”

Section: Scheme 14mentioning

confidence: 99%

The intermolecular Pictet-Spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically-active isoquinoline and indole alkaloids

Larghi¹,

Amongero²,

Bracca³

et al. 2005

Arkivoc

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“…That compound was thus ultimately isolated as the corresponding carboxylic acid. In contrast to selenium-stabilized alkyl carbocations, long known in the literature, vinyl carbocations have been largely overlooked and rarely explored or proposed as intermediates in organic synthesis . Therefore, in order to further elucidate the mechanism of the reaction, a computational study was carried out (Figure ).…”

mentioning

confidence: 99%

Redox-Neutral Synthesis of Selenoesters by Oxyarylation of Selenoalkynes under Mild Conditions

et al. 2018

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An approach for the mild synthesis of selenoesters starting from selenoalkynes through an acid-catalyzed, redox-neutral oxyarylation reaction is reported. Brønsted acid activation of a selenoalkyne leads to a selenium-stabilized vinyl cation, which is captured by an aryl sulfoxide and undergoes sigmatropic rearrangement to deliver the final α-arylated selenoester product. Computational studies have been carried out to elucidate the nature of the Se-stabilized carbocation.

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