Reaktionen mit <scp>L</scp>‐Cystinderivaten, II. Oxydierend‐chlorierende Spaltung und Darstellung von Sultam‐onen

Baganz, Horst; Dransch, Günter

doi:10.1002/cber.19600930406

Cited by 18 publications

(5 citation statements)

References 8 publications

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“…The oxidative cleavage (chlorinolysis) of cystine esters to give sulfur-free chloroesters has been reported (6, 7). The oxidation of bromide and iodide ions to the free halogen by N-haloimides forms the basis of a convenient method for the qualitative and quantitative identification of these ions (71,211,214).…”

Section: Carbon-oxygen Bondsmentioning

confidence: 99%

Oxidations and Dehydrogenations with N-Bromosuccinimide and Related N-Haloimides.

Filler¹

1963

Chem. Rev.

210

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Section: Carbon-oxygen Bondsmentioning

confidence: 99%

Oxidations and Dehydrogenations with N-Bromosuccinimide and Related N-Haloimides.

Filler¹

1963

Chem. Rev.

210

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“…[23] Highly enantioenriched O-sulfonylated b-hydroxysulfonamides 10 (R 2 = ortho-substituted aryl groups, method B) were prepared from enantiomerically pure planar chiral tricarbonyl-(h 6 -arene)chromium complexes. [24] For methods C) [25] and D) [26] efficient asymmetric versions are unknown.…”

Section: Introductionmentioning

confidence: 99%

“…Since the first reported preparation of b-sultams 1 in 1960, [6] their chemistry has been widely investigated not only because of the interesting biological properties, but also due to the usefulness of 1 as versatile reactive synthetic building blocks. [7] As four membered ring systems, b-sultams are highly strained species (CSN angle: ca.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of β‐Sultams as Precursors for Taurine Derivatives

Zajac

Peters

2009

Chemistry A European J

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Beta-sultams, biologically interesting sulfonyl analogues of beta-lactams, have been prepared by an organocatalytic asymmetric formal [2+2]-cycloaddition approach of non-nucleophilic imines with alkyl sulfonyl chlorides. In the case of very electron poor N-tosyl imines derived from chloral or ethylglyoxylate, this reaction type was catalyzed by cinchona alkaloids providing the heterocycles in high yield, with good diastereoselectivity and up to 94% ee. Mechanistic investigations suggested that the product formation proceeded via a zwitterionic imine-catalyst adduct. The scope was significantly extended by 2-pyridylsulfonyl imines derived from non-activated aromatic aldehydes employing Yb(OTf)3 as Lewis acid cocatalyst. The synthetic value of the strained enantioenriched beta-sultams was demonstrated by smooth nucleophilic ring opening reactions with O-, N- and C-nucleophiles yielding a variety of acyclic beta-aminosulfonyl (taurine) derivatives (sulfonates, sulfonamides, sulfones) without racemization or epimerization.

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“…l-Cystine dialkyl ester hydrochlorides 8, obtained from l-Cys, were transformed into the parent b-sultams 9a and 9b [10] by oxidative chlorination (Scheme 2). By thiol 41.…”

mentioning

confidence: 99%

Properties and Reactions of Substituted 1,2‐Thiazetidine 1,1‐Dioxides: Chiral Mono‐ and Bicyclic 1,2‐Thiazetidine 1,1‐Dioxides from α‐Amino Acids

Meinzer

Breckel

Thaher

et al. 2004

Helvetica Chimica Acta

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New chiral mono-and bicyclic b-sultams, valuable building blocks for drug synthesis, have been prepared from l-Ala, l-Val, l-Leu, l-Ile, l-Phe, l-Cys, l-Ser, l-Thr, and d-penicillamine by transformation of the COOH group into a methylsulfonyl chloride function, followed by cyclization under basic conditions. Selected properties, derivatives, and reactions of the b-sultams are described.Introduction. ± 1,2-Thiazetidine 1,1-dioxide (b-sultam) is a sulfone analogue (bioisoster) of the b-lactam moiety found in many important drugs [1]. It is known that the sultam ring is much more reactive than the b-lactam ring [2], and that b-sultams can interact with serine proteases such as elastase [3]. Therefore, b-sultams might be useful building blocks for new synthetic drugs and, therefore, should be available not only as racemic or diastereoisomeric mixtures, but as pure isomers [4]. Here, we report the synthesis and properties of chiral, stereochemically pure mono and bicyclic 3-substituted 1,2-thiazetidine 1,1-dioxides and their substitution products.A few examples of chiral b-sultams have been described in the literature [5]. For example, (R)-1,2-thiazetidine-3-carboxylic acid was obtained from l-Cys, and (R)-1,2-thiazetidine-3-methanol from l-Ser. In both cases, compounds from the natural −chiral pool× were used as starting materials, a general approach that has also been followed in the present paper.

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Reaktionen mit L‐Cystinderivaten, II. Oxydierend‐chlorierende Spaltung und Darstellung von Sultam‐onen

Cited by 18 publications

References 8 publications

Oxidations and Dehydrogenations with N-Bromosuccinimide and Related N-Haloimides.

Oxidations and Dehydrogenations with N-Bromosuccinimide and Related N-Haloimides.

Catalytic Asymmetric Synthesis of β‐Sultams as Precursors for Taurine Derivatives

Properties and Reactions of Substituted 1,2‐Thiazetidine 1,1‐Dioxides: Chiral Mono‐ and Bicyclic 1,2‐Thiazetidine 1,1‐Dioxides from α‐Amino Acids

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