A one-pot three-component synthesis of β-nitro-α-amino acids and their N-alkyl derivatives

Coghlan, Phillip A.; Easton, Christopher J.

doi:10.1039/a906223h

Cited by 9 publications

(5 citation statements)

References 8 publications

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“…One of the most traditional reactions categorized in this class is the Strecker reaction using HCN as a nucleophile (Scheme , eq 106) . Nevertheless, nucleophiles applicable to the reaction are limited to those bearing acidic protons, such as nitroalkanes (eq 107) and active methylene compounds (eq 108), Ugi-type reactions (eq 109), or pericyclic reactions (eq 110), due to the difficulties in selectively activating nucleophiles in an ammonium solution. To broaden the reaction scope and increase the reaction enantioselectivity, catalytic and selective activation of nucleophiles in the presence of a nitrogen source is indispensable.…”

Section: Reactions Involving N-unsubstituted Imines As Intermediatesmentioning

confidence: 99%

Recent Progress on Catalytic Addition Reactions toN-Unsubstituted Imines

2020

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Catalytic addition reactions to N-unsubstituted (N-unprotected) imines can provide a more straightforward synthesis of amines. This direct process eliminates the unnecessary protecting-group manipulations that are required with N-substituted (N-protected) imines and can contribute to the development of green chemistry. Although their use has been limited due to difficulties associated with the nature of N-unsubstituted imines, recently developed catalytic methods enable the use of N-unsubstituted imines as electrophiles in various catalytic addition reactions. To facilitate an understanding of the state of the art development of synthetic methodologies, herein we review recent progress on catalytic addition reactions to N-unsubstituted imines. We begin with an overview of the chemistry of N-unsubstituted imines, followed by a summary of recent progress categorized according to the reaction type. We hope this review will help to stimulate further development of greener syntheses of nitrogen-containing compounds.

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Section: Reactions Involving N-unsubstituted Imines As Intermediatesmentioning

confidence: 99%

Recent Progress on Catalytic Addition Reactions toN-Unsubstituted Imines

2020

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“…Imines derived from the reaction of primary amines and glyoxylic acid are well known and characterised 8 and have been exploited as reactive intermediates in tandem reaction processes including the Diels-Alder reaction 9 and nucleophilic additions of nitro alkanes. 10 The action of imines as nucleophiles is less frequently utilised as a synthetic technique, although is well established in, for example, N-acyliminium chemistry. 11 Within the examination of the scope of the reaction we confirmed that both secondary (Table 2, entry 9) and tertiary amines (Table 2, entry 10) were returned unreacted after exposure to the standard reaction conditions.…”

Section: Prmentioning

confidence: 99%

A Mild and Efficient Method for the One-Pot Monocarboxymethylation of Primary Amines

Gibbs¹,

Boomhoff²,

Tomkinson

2007

Synlett

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M o n o c a r b o x y m e t h y l a t i o n o f P r i m a r y A m i n e sAbstract: A mild and efficient method for the monocarboxymethylation of primary amines that takes place under aqueous conditions at room temperature is described. Treatment of an aqueous solution of a variety of primary amines with two equivalents of glyoxylic acid leads to the N-formyl glycine derivatives. Direct hydrolysis of the crude reaction solution leads to the products of amine monocarboxymethylation in good to excellent yield.

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“…Electrospray (ESI) mass spectra were obtained using a VG Quatro II triple quadrupole mass spectrometer operating in the positive ion mode. β-Nitroalanine 6a, 7 β-nitrovaline 6b, 8 β-nitrocyclopentylglycine 6c 8 and N-methyl-β-nitronorvaline 6d 8d were prepared as reported previously, the latter as a 6:1 mixture of…”

Section: Methodsmentioning

confidence: 99%

“…β-Nitro amino acids with a wide variety of side chains are easily prepared through reaction of α-bromoglycine derivatives with alkyl nitronates 6,7 or, more directly, through the three-component coupling of amines, nitroalkanes and glyoxylate in aqueous base. 8 Previously we have shown that the amino acid tert-butyl esters can be incorporated as the C-terminal residues in N-and C-protected dipeptides, using solution-phase methods. 9 We now report on the utility of the nitro amino acids in solid-phase peptide synthesis, and the isolation and characterization of the free peptides.…”

Section: Introductionmentioning

confidence: 99%

β-Nitro-α-amino acids as latent α,β-dehydro-α-amino acid residues in solid-phase peptide synthesis

Coghlan¹,

Easton²

2004

Arkivoc

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β-Nitro-α-amino acids, that are readily accessible through either the reaction of bromoglycine derivatives with alkyl nitronates or the three-component coupling of amines, nitroalkanes and glyoxalate in aqueous base, are easily converted to the corresponding N-t-Boc-amino acids. These undergo solid-phase Merrifield peptide synthesis, with elimination of nitrous acid, either during or subsequent to cleavage of the peptide from the resin, converting the nitro amino acids to dehydro amino acid residues. The method has been applied successfully with two β,β-disubstituted nitro amino acids and N-methyl-β-nitronorvaline, but failed with β-nitroalanine.

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A one-pot three-component synthesis of β-nitro-α-amino acids and their N-alkyl derivatives

Cited by 9 publications

References 8 publications

Recent Progress on Catalytic Addition Reactions toN-Unsubstituted Imines

Recent Progress on Catalytic Addition Reactions toN-Unsubstituted Imines

A Mild and Efficient Method for the One-Pot Monocarboxymethylation of Primary Amines

β-Nitro-α-amino acids as latent α,β-dehydro-α-amino acid residues in solid-phase peptide synthesis

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