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The synthesis of S 18986, a chiral AMPA receptor modulator, via catalytic asymmetric hydrogenation

✍ Scribed by Christopher J. Cobley; Elsa Foucher; Jean-Pierre Lecouve; Ian C. Lennon; James A. Ramsden; Gilles Thominot

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
156 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

The asymmetric hydrogenation of a dihydropyrrolo-benzothiadiazine dioxide 1 with a diphosphine ruthenium diamine catalyst has been used to synthesize the AMPA receptor positive modulator tetrahydropyrrolo-benzothiadiazine dioxide 2 (S 18986) in high enantiomeric excess. The use of factorial experimental design led to significant improvements in the process parameters and improved enantioselectivity.

πŸ“œ SIMILAR VOLUMES

Enantioselective synthesis of a pyrrolo-
Enantioselective synthesis of a pyrrolo-benzothiadiazine derivative S 18986, a new AMPA receptor positive modulator
✍ P. Desos; B. Serkiz; P. Morain; J. Lepagnol; A. Cordi πŸ“‚ Article πŸ“… 1996 πŸ› Elsevier Science 🌐 English βš– 314 KB

Enantioselective reduction of pyrrolo-benzothiadiazine 6 using various chiral reducing agents has been studied and led to efficient synthesis of 8 (S 18986) which was established to be of (S) configuration by single crystal X-ray diffraction analysis. S 18986 is a potent and selective AMPA positive

Approach to the stereoselective synthesi
Approach to the stereoselective synthesis of (R)- and (S)-4-methoxydalbergione via asymmetric catalytic hydrogenation
✍ Philippe Bissel; RafaΓ«l Sablong; Jean-Pierre Lepoittevin πŸ“‚ Article πŸ“… 1995 πŸ› Elsevier Science 🌐 English βš– 227 KB

Compound 7, a precursor in the synthesis of 4-methoxybalbergione, was prepared from compound 6 with an enantiomeric excess of 17 to 94% by asymmetric catalytic hydrogenation using rhodium or ruthenium chiral complexes. The best hydrogenation results were obtained using [Rh((S,S)-bdpp)(NBD)1 Cl04, an