Synthesis of Tertiary β-Hydroxy Amides by Enolate Additions to Acylsilanes

Lettan, Robert; Reynolds, Troy E.; Galliford, Chris V.; Scheidt, Karl A.

doi:10.1021/ja065605v

Cited by 47 publications

(16 citation statements)

References 21 publications

(10 reference statements)

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“…With the established procedure in hand ( Table 1, entry 11), the generality of this transformation for the synthesis of b-amino amides was next explored using a variety of N-tosyl-substituted aldimines 2 b-2 i and vinyl azide 1 a (Scheme 5). [19] Various aromatic aldimines 2 b-2 g, including those with indolyl or benzofuranyl moieties, could be utilized to give the corresponding b-amino amides 3 ab-3 ag in good to excellent yields. The reaction with a,b-unsaturated aldimine 2 h resulted in the 1,2-addition product 3 ah in 53 % yield.…”

supporting

confidence: 67%

Amide Synthesis by Nucleophilic Attack of Vinyl Azides

Zhang¹,

Wang²,

Lonca³

et al. 2014

Angewandte Chemie

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A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enaminetype nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF 3 ·OEt 2 . After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide. Scheme 1. Amide synthesis with organic azides. Scheme 2. Protonation of vinyl azides for the formation of amides. Scheme 6. Reactions with aldehydes 4 a and 4 b. Scheme 7. Scope of a-aryl vinyl azides 1. Scheme 8. Reaction with a-alkyl-substituted vinyl azide 1 h. Scheme 9. Reactions of cyclic vinyl azides 1 i and 1 j.

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supporting

confidence: 67%

Amide Synthesis by Nucleophilic Attack of Vinyl Azides

Zhang¹,

Wang²,

Lonca³

et al. 2014

Angewandte Chemie

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“…In 2006, Scheidt reported a multicomponent reaction involving a lithium homoenolate derived from a 1,2‐Brook rearrangement (Scheme ) . After deprotonation of 158 , treatment with 159 gives 162 .…”

Section: Homoenolates As Nucleophilic Reagentsmentioning

confidence: 99%

Modern Developments in the Chemistry of Homoenolates

Mills

Rousseaux

2018

Eur J Org Chem

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Homoenolates are unique synthetic intermediates which display umpolung reactivity. Homoenolates and homoenolate equivalents like cyclopropanols have seen a recent surge in popularity due to their particular utility for accessing β‐functionalized carbonyl derivatives. This popularity has been enabled by the development of protocols for facile access to cyclopropanols and homoenolates from a variety of readily available starting materials. This microreview will highlight common strategies for generating cyclopropanols and metal homoenolates, as well as procedures for homoenolate functionalization, with a particular emphasis on protocols that have appeared after 2003. As an amphoteric molecule, two main reactivity modes have been established: the homoenolate reacts as a carbon nucleophile for β‐functionalization reactions and/or as a carbonyl electrophile, a strategy which has only emerged in the past few years. This microreview will highlight the use of homoenolates as convenient intermediates for accessing especially challenging motifs. The use of homoenolate chemistry in the context of natural product and pharmaceutical synthesis will also be presented.

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“…[4] New types of catalysts have also been developed with regard to the activation of acylsilanes in 1,2-benzointype additions and 1,4-Stetter reactions, e.g., thiazolium salts, [5] cyanides [6] and metallophosphites. [7] More recently, new applications of acylsilanes have been established with the addition of enolates, [8] Pd-catalyzed coupling reactions, [9] synthesis of substituted g-lactams, [10] or photochemical transformations.…”

Section: Acylsilanes [Rcosi(r')mentioning

confidence: 99%

Synthesis of Acylsilanes by Copper(I)‐Catalyzed Addition of Silicon Nucleophiles onto Acid Derivatives

Cirriez¹,

Rasson²,

Riant³

2013

Adv Synth Catal

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The transition metal-catalyzed transfer of silicon nucleophiles onto various electrophiles has recently gained considerable attention, due to the now readily available silicon pro-nucleophiles such as silylboronates. Our interest lies in the addition of such species to acid derivatives for the generation of acylsilanes. We report herein an efficient method to synthesize these compounds, starting from easyto-form anhydrides, with very good yields.

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Synthesis of Tertiary β-Hydroxy Amides by Enolate Additions to Acylsilanes

Cited by 47 publications

References 21 publications

Amide Synthesis by Nucleophilic Attack of Vinyl Azides

Amide Synthesis by Nucleophilic Attack of Vinyl Azides

Modern Developments in the Chemistry of Homoenolates

Synthesis of Acylsilanes by Copper(I)‐Catalyzed Addition of Silicon Nucleophiles onto Acid Derivatives

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