Zur Reduktion von 1,2‐Thiazetidin‐1,1‐dioxiden. Reduction of 1,2‐Thiazetidine 1,1‐Dioxides

Meyle, Eberhard; Otto, Hans‐Hartwig

doi:10.1002/ardp.19873200618

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Cited by 5 publications

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ChemInform Abstract: Reduction of 1,2‐Thiazetidine 1,1‐Dioxides.

Meyle

Otto

1987

ChemInform

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168ChemInform Abstract The β-sultams (I) are reductively cleaved with a complex aluminum hydride, yielding the aminomercaptans (II). During the conversion of the benzoyl derivative (Id), the carbonyl group is simultaneously reduced to give the corresponding benzylic compound (IId). The dicarbonyl-bridged bissultam (III) is transformed into N,N'-di(2-mercaptoethyl)ethylenediamine (IV) using the same method.

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ChemInform Abstract: Reduction of 1,2‐Thiazetidine 1,1‐Dioxides.

Meyle

Otto

1987

ChemInform

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Properties and reactions of substituted 1,2‐thiazetidine 1,1‐dioxides: Acylation of β‐sultams at C‐4, reduction of 4‐acyl‐β‐sultams, and stereochemistry of 4‐(α‐hydroxyalkyl)‐β‐sultams

Müller

Otto

1991

Liebigs Ann. Chem.

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Acylation of N‐silylated and 2,3‐substituted 1,2‐thiazetidine 1,1‐dioxides (β‐sultams) results in the formation of 4‐acylated β‐sultams 2 and 8. The desilylation of 2 to 3 is easily done with TBAF either on silica gel or in ethanolic solution. The acylated β‐sultams are reduced by sodium borohydride yielding α‐hydroxyalkyl β‐sultams 11 and 12, obtained as mixtures of diastereoisomers. These are separated by CC. The stereochemistry of the acylated and of the α‐hydroxylated β‐sultams is elucidated by spectroscopic methods, and compared to that of the antibiotic drug thienamycin.

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Four-membered Rings with One Sulfur and One Nitrogen Atom

Harris

1996

Comprehensive Heterocyclic Chemistry II

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Zur Reduktion von 1,2‐Thiazetidin‐1,1‐dioxiden. Reduction of 1,2‐Thiazetidine 1,1‐Dioxides

Cited by 5 publications

References 16 publications

ChemInform Abstract: Reduction of 1,2‐Thiazetidine 1,1‐Dioxides.

ChemInform Abstract: Reduction of 1,2‐Thiazetidine 1,1‐Dioxides.

Properties and reactions of substituted 1,2‐thiazetidine 1,1‐dioxides: Acylation of β‐sultams at C‐4, reduction of 4‐acyl‐β‐sultams, and stereochemistry of 4‐(α‐hydroxyalkyl)‐β‐sultams

Four-membered Rings with One Sulfur and One Nitrogen Atom

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