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Asymmetric synthesis of (1R,2S)-2-fluorocyclopropylamine, the key intermediate of the new generation of quinolonecarboxylic acid, DU-6859

✍ Scribed by Osamu Tamura; Masaru Hashimoto; Yuko Kobayashi; Tadashi Katoh; Kazuhiko Nakatani; Masahiro Kamada; Isao Hayakawa; Toshifumi Akiba; Shiro Terashima


Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
311 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis


The title synthesis was achieved by featuring diastereoface selective cyclopropanation of (4RE%4.5diphenyl-3-vinyl-2-oxazolidinonc. the chiral and conformationally rigid N-vinylcarbamate, with zincmonofuorocarbenoid followed by hydrogenolysis of formed (4R~S)-3-[(1R2S)-2-fluorocyclopropylI~5-diphenyl-2oxawlidinone.


πŸ“œ SIMILAR VOLUMES


Synthetic studies on the key component o
✍ Toshifumi Akiba; Osamu Tamura; Masaru Hashimoto; Yuko Kobayashi; Tadashi Katoh; πŸ“‚ Article πŸ“… 1994 πŸ› Elsevier Science 🌐 French βš– 910 KB

## The title synthesis was achieved by featuring diastereoface-selective cyclopropanation of (4R,5S)-4Jdiphenyl-3-vinyl-2-oxazolidinone and its related compounds, the chiral conformationally rigid N-vinylcarbamates, with sine-monojluorocarbenoid, followed by hydrogenolysis of the major addition prod

Synthesis and optical resolution of dl-c
✍ Osamu Tamura; Masaru Hashimoto; Yuko Kobayashi; Tadashi Katoh; Kazuhiko Nakatani πŸ“‚ Article πŸ“… 1992 πŸ› Elsevier Science 🌐 French βš– 276 KB

The title synthesis was accomplished by featuring highly cis-selective cyclopropanation of an Nvinylcarbamate with zinc-monofluorocarbenoid followed by deprotection of the formed N-(cis-2fluorocyclopropyl)m&amate. Optical resolution of~-cis-2-~~ro~clopropyhnrinc was also achiewd by employing lmenthy

Asymmetric Synthesis via Heterocyclic In
✍ Groth, Ulrich ;Halfbrodt, Wolfgang ;SchΓΆllkopf, Ulrich πŸ“‚ Article πŸ“… 1992 πŸ› John Wiley and Sons 🌐 English βš– 518 KB

## Abstract __allo__‐Coronamic acid (1) was synthesized in five steps enantiomerically and diastereomerically virtually pure by starting from the bislactim ethers of cyclo(‐L‐Val‐Gly‐) (3a) or cyclo‐(‐L‐__tert__‐Leu‐Gly‐) (3b) in an overall yield of 31%. The key step of this synthesis is the intram

1,3-Asymmetric induction in the intramol
✍ Pil-Jong Shim; Hee-Doo Kim πŸ“‚ Article πŸ“… 1998 πŸ› Elsevier Science 🌐 French βš– 244 KB

Optically active bicyclo[4.2.0]octan-7-ones were synthesized by stereoselective intramolecular [2+2] cycloaddition of alkene-keteniminium salt derived from L-glutamic acid, based on 1,3-asymmelric induction. Synthetic application toward (+)-gibberellic acid key intermediate was also described.