New Synthesis of .alpha.-Amino Acid N-Carboxy Anhydrides through Baeyer-Villiger Oxidation of .alpha.-Keto .beta.-Lactams

Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Carreaux, François; Cuevas, Carmen; Maneiro, E.; Ontoria, J. M.

doi:10.1021/jo00090a033

Cited by 46 publications

(18 citation statements)

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“…Subsequent oxidations were performed by treatment with DMSO in the presence of phosphorous pentoxide [14] to give the α-keto-β-lactams (1a-g) in good yields as shown in Scheme 4. …”

Section: Resultsmentioning

confidence: 99%

An Efficient and Simple Procedure for the Preparation of α-Keto-β-lactams

2000

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585α-Keto-β-lactams 1 are at the crossroads of many important transformations leading to bioactive compounds [1]. Recently, we used yeast-catalyzed reduction of 1-(4-methoxyphenyl)-4-phenyl-2,3-azetidindione as a key step in a biocatalytic approach to the synthesis of the paclitaxel C-13 side chain (Scheme 1) [2]. To investigate other 4-substituted α-keto-β-lactams as substrates for microbial reductions and subsequent conversions to optically pure C-13 side-chain analogs we required a simple, efficient, and general protocol for the synthesis of these compounds.Abstract. The methods for the preparation of α-keto-β-lactams described in the literature are generally specific for a particular target molecule and lack generality. A short route to several of these compounds has been developed and is deods, therefore, are suitable only for the preparation of compounds with acid-resistant substituents. Thus, low reactivity of the quaternary center in the intermediates A, B, or C (the latter accessible via cyclization of a thio-precursor followed by chlorination) towards nucleophilic attack limits the applicability of these otherwise simple and straightforward syntheses.scribed in this communication. The protocol based on an efficient cyclization procedure followed by hydrolysis and oxidation allows preparation of α-keto-β-lactams 5a -g with sensitive substituents.

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“…Subsequent oxidations were performed by treatment with DMSO in the presence of phosphorous pentoxide [14] to give the α-keto-β-lactams (1a-g) in good yields as shown in Scheme 4. …”

Section: Resultsmentioning

confidence: 99%

An Efficient and Simple Procedure for the Preparation of α-Keto-β-lactams

2000

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“…In particular, enantiopure 3-hydroxy-4-(aminoalkyl) b-lactams 97, readily available from acid chlorides 96 and optically pure a-amino imines 95, were efficiently submitted to an oxidative cycloexpansion protocol using TEMPO (2,2,6,6-tetramethylpiperidinooxy) that provides N-carboxy anhydrides 98 without epimerization. Ensuing esterification rendered enantiopure differentially protected syn a,b-diamino esters 99 [69].…”

Section: Electrophilic Synthetic Equivalents Of Co 2 R and Other Apprmentioning

confidence: 99%

Synthetic Approaches to α,β‐Diamino Acids

Viso

Pradilla

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…They have been widely used for the synthesis of -amino acid derivatives [3,4] and -amino acid derivatives [5,6] via ring-opening reactions. They have also been applied in the preparation of heterocycles [718], polycyclic heterocyclic compounds [1925], alkaloids [23,26], antibiotics [2731], and even more complex natural products [23,32] via ring enlargements.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis of cis- and trans-4-acyl-β-lactams from vicinal diketones and ketoaldehydes

Wang

2011

Sci. China Chem.

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4-Acyl--lactams are important synthetic intermediates in both pharmaceutical and organic chemistry. Cis-and trans-4-acyl--lactams were synthesized stereoselectively from vicinal diketones via the formation of bulky and less bulky diimines as key intermediates, respectively. The diimines reacted with acyl chloride in the presence of triethylamine to give rise to the corresponding 4-imino--lactams, which were further hydrolyzed to afford 4-acyl--lactams. The cis-and trans selectivity is depended on the steric hindrance of the imine N-substituents. A series of cis-4-acyl--lactams were synthesized from vicinal ketoaldehydes via the formation of their monoimines and diimines as intermediates. Pyruvic aldehyde produced cis-4-acetyl--lactams and cis-4-formyl--lactams, respectively, through the reactions of its monoimine and diimine with acyl chlorides. Phenylglyoxal generated cis-4-benzoyl--lactams via its monoaldimine. 4-acyl--lactam, diimine, diketone, imine, ketoaldehyde, -lactam, stereoselectivity

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New Synthesis of .alpha.-Amino Acid N-Carboxy Anhydrides through Baeyer-Villiger Oxidation of .alpha.-Keto .beta.-Lactams

Cited by 46 publications

References 0 publications

An Efficient and Simple Procedure for the Preparation of α-Keto-β-lactams

An Efficient and Simple Procedure for the Preparation of α-Keto-β-lactams

Synthetic Approaches to α,β‐Diamino Acids

Stereoselective synthesis of cis- and trans-4-acyl-β-lactams from vicinal diketones and ketoaldehydes

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