Stereoselektive Metall‐freie Synthese von β‐Aminothioestern mit tertiären und quartären Stereozentren

Bahlinger, Annette; Fritz, Sven; Wennemers, Helma

doi:10.1002/ange.201310532

Cited by 15 publications

(1 citation statement)

References 41 publications

(35 reference statements)

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“…A drawback of this method is the difficulties to introduce a substituent at the α ‐position of the β ‐amino acid derivatives. Notably, very recently Wennemers’ group successfully overcame this challenge by using monothiomalonates as the substrates and aliphatic groups were successfully attached to the α ‐position of the amino group 8a…”

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confidence: 99%

Controlling the Reactivity of the SeSe Bond by the Supramolecular Chemistry of Cucurbituril

et al. 2014

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We describe a new strategy to control the reactivity of SeSe bond by using supramolecular chemistry of cucurbituril. We have demonstrated that selenocystamine (SeCy) and cucurbit[6]uril (CB[6]) can form a stable supramolecular complex (Ka =5.5×10(6) M(-1) ). Before complexation, the free SeSe bond in SeCy is rather sensitive to redox stimuli and gets disrupted quickly with addition of reductant or oxidant. However, after binding with CB[6], the SeSe bond becomes quite inert and hardly reacts with reductant or oxidant. One advantage of this supramolecular protection is that it can be applied in a wide pH range from weakly acidic to basic. Additionally, the supramolecular complex formed by SeCy and CB[6] can be reversibly dissociated simply with addition of Ba(2+) .

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Section: Introductionmentioning

confidence: 99%

Controlling the Reactivity of the SeSe Bond by the Supramolecular Chemistry of Cucurbituril

et al. 2014

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Stereoselective Mannich Reaction of S‐Phenyl Thioesters Catalyzed by Bifunctional Organocatalysts

2014

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Stereoselective Organocatalytic Synthesis of Oxindoles with Adjacent Tetrasubstituted Stereocenters

2015

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Oxindoles with adjacent tetrasubstituted stereocenters were obtained in high yields and stereoselectivities by organocatalyzed conjugate addition reactions of monothiomalonates (MTMs) to isatin-derived N-Cbz ketimines.T he method requires only al ow catalyst loading (2 mol %) and proceeds under mild reaction conditions.Both enantiomers are accessible in good yields and excellent stereoselectivities by using either Takemotos catalyst or ac inchona alkaloid derivative.T he synthetic methodology allowed establishment of as traightforwardr oute to derivatives of the gastrin/ cholecystokinin-B receptor antagonist AG-041R.

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Stereoselektive Metall‐freie Synthese von β‐Aminothioestern mit tertiären und quartären Stereozentren

Cited by 15 publications

References 41 publications

Controlling the Reactivity of the SeSe Bond by the Supramolecular Chemistry of Cucurbituril

Controlling the Reactivity of the SeSe Bond by the Supramolecular Chemistry of Cucurbituril

Stereoselective Mannich Reaction of S‐Phenyl Thioesters Catalyzed by Bifunctional Organocatalysts

Stereoselective Organocatalytic Synthesis of Oxindoles with Adjacent Tetrasubstituted Stereocenters

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