A flexible method for the synthesis of 2-substituted 1,2,5,6-tetrahydropyridines and piperidines from chloro-containing propargylamines

Penk, Danielle N; Robinson, Nathan A.; Hill, Harrison; Turlington, Mark

doi:10.1016/j.tetlet.2016.12.061

Cited by 8 publications

(2 citation statements)

References 25 publications

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“…There are many compounds with a 1,2,3,4-tetrahydroisoquinoline structural motif bearing substituents at 1-position which display a wide range of biological activities. However, Turlington and co-workers reported a stereoselective synthesis in three steps of 2-substituted 1,2,5,6-tetrahydropyridines 196 starting from chiral N-tert-butanesulfinyl imines (R S )-14 [139]. The synthesis commenced with addition of the organolithium compound resulting from the deprotonation of 4-chloro-1butyne (194) to the imine.…”

Section: Cyclizations Involving a Position In The Attacking Nucleophilementioning

confidence: 99%

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Mendes¹,

Costa²,

Yus³

et al. 2021

Beilstein J. Org. Chem.

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The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from tert-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format.

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Section: Cyclizations Involving a Position In The Attacking Nucleophilementioning

confidence: 99%

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Mendes¹,

Costa²,

Yus³

et al. 2021

Beilstein J. Org. Chem.

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“…The direct formation of lithium acetylides has been applied to ynamides [31] or 4‐chlorobutyne ( 36 ) [32] in the reaction with imines 16 . In the second case the, obtained products 37 were easily transformed into chiral tetrahydropyridines by intramolecular S N reaction in the presence of a base (Scheme 15).…”

Section: Organoalkaline Compoundsmentioning

confidence: 99%

Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

Foubelo

Yus

2020

The Chemical Record

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In this account the reactions of chiral N‐tert‐butylsulfinyl imines with organometallic reagents such as organoalkaline (lithium, sodium, potassium and cesium derivatives), organomagnesium, organozinc, organoboron, organoaluminium, organoindium and organosilicon compounds is comprehensively described. The reactivity in all cases is derived to synthetic applications in order to prepare interesting organic nitrogenated molecules, especially in the field of alkaloid compounds.

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Ionic Liquid-Attached Colloidal Silica Nanoparticles as a New Class of Silica Nanoparticles for the Preparation of Propargylamines

Safaei‐Ghomi

Nazemzadeh

2017

Catal Lett

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A flexible method for the synthesis of 2-substituted 1,2,5,6-tetrahydropyridines and piperidines from chloro-containing propargylamines

Cited by 8 publications

References 25 publications

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

Ionic Liquid-Attached Colloidal Silica Nanoparticles as a New Class of Silica Nanoparticles for the Preparation of Propargylamines

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