Highly Stereoselective Synthesis of β‐Lactams Utilizing α‐Chloroimines as New and Powerful Chiral Inductors

D’hooghe, Matthias; Brabandt, Willem Van; Dekeukeleire, S.; Dejaegher, Yves; Kimpe, Norbert De

doi:10.1002/chem.200800845

Cited by 30 publications

(18 citation statements)

References 47 publications

(41 reference statements)

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“…The separated solid was filtered, and then recrystallized from suitable solvent ethanol: water (7:3). Table (2) lists physical properties and FT-IR spectral data of Schiff bases (3)(4)(5)(6).…”

Section: Synthesis Of Schiff Bases (3-6) [13]mentioning

confidence: 99%

“…The most important four-member system is undoubtedly the azetidin-2-one, also called β-lactam. βlactam contaning compounds have a wide spectrum antibiotic which found in natural and synthetic compounds, such as penicillin, cephalosporin, carbaphenems, and monobactams [4,5]. The chemistry of carbonnitrogen double bond plays a vital role in the progresses of chemistry science [6].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of New Some Imidazole Derivatives Containing ?-Lactam Ring

Journal¹

2016

Baghdad Sci.J

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In this work 5-methylene-yl - (2-methy –oxazole-4-one) (1H) imidazole (1) were synthesized from the reaction of L-Histidine with acetic anhydride and which converted to the of 5-methylene-yl-(2-methyl 3-amino imidazole-4-one)-1H-imidazole (2) by reaction with hydrazine hydrate. Schiff bases (3-6) were synthesized from the reaction of compound (2) with different aromatic aldehyde. Reaction of compounds (3-6) with chloroacetyl chloride gives azetidinone one derivatives (7-10). These compounds were characterized by FT-IR and some of them with 1H-NMR and 13C-NMR spectroscopy.

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Section: Synthesis Of Schiff Bases (3-6) [13]mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of New Some Imidazole Derivatives Containing ?-Lactam Ring

Journal¹

2016

Baghdad Sci.J

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“…37 An oxidation of alcohol 35 with pyridinium cholorochromate (PCC) afforded the corresponding aldehyde which on treatment with 1 equivalent of amines yielded the (S)-N-(2-chloropropylidene)amines 36. The reaction of azomethines 36 with benzyloxy-or methoxyacetyl chloride 33 under Staudinger conditions gave the corresponding 2-azetidinones (Scheme 11).…”

Section: Scheme 10mentioning

confidence: 99%

Advances in synthesis of monocyclic beta-lactams

Singh¹,

Sudheesh²

2014

Arkivoc

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Recent years have witnessed significant advancement in cycloaddition and cyclization strategies for the synthesis of monocyclic β-lactams. Cycloadditions include the Staudinger's keteneimine cycloaddtions and related reaction. Cyclization reactions are reported to furnish β-lactams through N 1 -C 2 , N 1 -C 4 and C 3 -C 4 bond formations employing substrates like β-amino esters, β-amino alcohols, β-hydroxamate esters, and α-amino diazocarbonyls, etc. Some other strategies are silyl carbonylation reactions, ring-enlargement of aziridines, cleavage of one ring of a bicyclic β-lactam, and functional group transformations on the β-lactam rings. Recently, some multi-component reactions have also been designed. This article reviews the advances made in synthetic approaches to monocyclic β-lactams during last five years.

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“…To obtain 4-(1-chloroethyl)azetidin-2-ones 8, 2(S)-chloro-1-propanol 7 was chosen as substrate for oxidation with pyridinium chlorochromate (PCC) to 2(S)-chloropropanal, further imination with primary amines and Staudinger reaction. In this way, chiral 4-(1-chloroethyl)azetidin-2-ones 8 were prepared for the first time in a one-pot synthesis in high diastereomeric excess (80-89 %) and overall yields of 19-43 % (except for the 3-methoxy derivative in 6 %) (Scheme 2) [10]. The enantiomeric excess was shown to be 90 % through coupling of β-lactam 8 (R 1 = Bu, R 2 = Bn) with (R)-α-methoxy-α-trifluoromethyl phenylacetic acid and subsequent GC analysis.…”

Section: Synthesis Of 4-(haloalkyl)azetidin-2-onesmentioning

confidence: 99%

Use of functionalized β-lactams as building blocks in heterocyclic chemistry

D’hooghe

Dekeukeleire

Leemans

et al. 2010

Pure and Applied Chemistry

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β-Lactams represent flexible building blocks suitable for the preparation of a large variety of nitrogen-containing target compounds. In the present study, the formerly neglected synthetic potential of 4-haloalkyl-β-lactams has been elaborated in detail with a focus on the preparation of different mono-and bicyclic heterocycles. A first approach involved ring transformations of these halogenated building blocks toward stereodefined aziridines, azetidines, pyrrolidines, and piperidines via intermediate aziridinium or azetidinium ions. In a second part, novel and stereoselective entries into 1,4-and 3,4-fused bicyclic β-lactams were developed through either a radical or an ionic cyclization protocol. Furthermore, the ring enlarge ment of halogenated β-lactams into functionalized mono-and bicyclic pyrrolidin-2-ones was established as the aza-analog of the cyclobutylmethylcarbenium ion to cyclopentylcarbenium ion rearrangement. Finally, chiral versions toward azetidin-2-ones and ring transformation products were elaborated, involving the synthesis of 3(S)-alkoxy-4(S)-[1(S)-chloroethyl]azetidin-2-ones and the preparation of bicyclic β-lactams annelated to piperazines, morpholines, and diazepanes.

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Highly Stereoselective Synthesis of β‐Lactams Utilizing α‐Chloroimines as New and Powerful Chiral Inductors

Abstract: A new and efficient one‐pot approach towards chiral azetidin‐2‐ones has been developed starting from (2S)‐chloro‐1‐propanol, affording novel β‐lactams in high diastereomeric (80–89 %) and enantiomeric excess (90 %).

Cited by 30 publications

References 47 publications

Synthesis of New Some Imidazole Derivatives Containing ?-Lactam Ring

Synthesis of New Some Imidazole Derivatives Containing ?-Lactam Ring

Advances in synthesis of monocyclic beta-lactams

Use of functionalized β-lactams as building blocks in heterocyclic chemistry

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