local anesthetic azabicyclo-N-alkylanilides

Bever, Willem F. M. Van; Knaeps, A. G.; Willems, Johan J. M.; Hermans, Bert; Janßen, Paul

doi:10.1021/jm00262a019

Cited by 9 publications

(1 citation statement)

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“…Rodocaine is an important chemical that is used in ophthalmic anesthesia [94][95][96]. There are a number of methods that have been developed for the synthesis of this molecule.…”

Section: Rodocainementioning

confidence: 99%

The Corey-Seebach Reagent in the 21st Century: A Review

et al. 2023

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The Corey-Seebach reagent plays an important role in organic synthesis because of its broad synthetic applications. The Corey-Seebach reagent is formed by the reaction of an aldehyde or a ketone with 1,3-propane-dithiol under acidic conditions, followed by deprotonation with n-butyllithium. A large variety of natural products (alkaloids, terpenoids, and polyketides) can be accessed successfully by utilizing this reagent. This review article focuses on the recent contributions (post-2006) of the Corey-Seebach reagent towards the total synthesis of natural products such as alkaloids (lycoplanine A, diterpenoid alkaloids, etc.), terpenoids (bisnorditerpene, totarol, etc.), polyketide (ambruticin J, biakamides, etc.), and heterocycles such as rodocaine and substituted pyridines, as well and their applications towards important organic synthesis.

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“…Rodocaine is an important chemical that is used in ophthalmic anesthesia [94][95][96]. There are a number of methods that have been developed for the synthesis of this molecule.…”

Section: Rodocainementioning

confidence: 99%

The Corey-Seebach Reagent in the 21st Century: A Review

et al. 2023

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Enantioselective Hydroazidation of Trisubstituted Non‐Activated Alkenes

Meyer

Renaud

2017

Angewandte Chemie

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Aone-pot procedure for the enantioselective hydroazidation of non-activated trisubstituted alkenes is described. Hydroboration with monoisopinocampheylborane (IpcBH 2 ) provides dialkylboranes that are in situ selectively converted into monoalkyl-substituted catecholboranes;t hese undergo radical azidation upon treatment with benzenesulfonyl azide and ar adical initiator.E nantiomerically enriched azides were thus obtained in yields of 59-81 %a nd enantioselectivities of up to 94:6 e.r. (98:2 e.r. if the intermediate dialkylborane is purified by crystallization). Arapid access to enantiomerically pure (+ +)-rodocaine is also described. The use of other arenesulfonyl radical traps enables enantioselective hydroallylation, hydrosulfanylation, and hydrobromination reactions with yields of 71-86 %.

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Regio‐ and Diastereoselective [3+2] Annulation of Aliphatic Aldimines with Alkenes by Scandium‐Catalyzed β‐C(sp³)−H Activation

et al. 2021

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Here we report for the first time the regio-and diastereoselective [3+2] annulation of a wide range of aliphatic aldimines with alkenes via the activation of an unactivated β-C(sp 3 )À H bond by half-sandwich scandium catalysts. This protocol offers a straightforward and atomefficient route for the synthesis of a new family of multisubstituted aminocyclopentane derivatives from easily accessible aliphatic aldimines and alkenes. The annulation of aldimines with styrenes exclusively afforded the 5-aryl-transsubstituted 1-aminocyclopentane derivatives with excellent diastereoselectivity through the 2,1-insertion of a styrene unit. The annulation of aldimines with aliphatic alkenes selectively gave the 4-alkyl-trans-substituted 1-aminocyclopentane products in a 1,2-insertion fashion. A catalytic amount of an appropriate amine such as adamantylamine (AdNH 2 ) or dibenzylamine (Bn 2 NH) showed significant effects on the catalyst activity and stereoselectivity.

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local anesthetic azabicyclo-N-alkylanilides

Cited by 9 publications

References 0 publications

The Corey-Seebach Reagent in the 21st Century: A Review

The Corey-Seebach Reagent in the 21st Century: A Review

Enantioselective Hydroazidation of Trisubstituted Non‐Activated Alkenes

Regio‐ and Diastereoselective [3+2] Annulation of Aliphatic Aldimines with Alkenes by Scandium‐Catalyzed β‐C(sp³)−H Activation

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local anesthetic azabicyclo-N-alkylanilides

Cited by 9 publications

References 0 publications

The Corey-Seebach Reagent in the 21st Century: A Review

The Corey-Seebach Reagent in the 21st Century: A Review

Enantioselective Hydroazidation of Trisubstituted Non‐Activated Alkenes

Regio‐ and Diastereoselective [3+2] Annulation of Aliphatic Aldimines with Alkenes by Scandium‐Catalyzed β‐C(sp3)−H Activation

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Product

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Regio‐ and Diastereoselective [3+2] Annulation of Aliphatic Aldimines with Alkenes by Scandium‐Catalyzed β‐C(sp³)−H Activation