𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of enantiomerically pure 2,3-disubstituted isoxazolidin-5-ones

✍ Scribed by Irma Panfil; Sylwester Maciejewski; Czesław Bełzecki; Marek Chmielewski

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
151 KB
Volume
30
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Conjugate addition-rearrangement of N-substituted hydroxylamines sugar &lactones provides a short and effective route to title compounds. to cr,8-unsaturated Despite the interesting heterocyclic skeleton of isoxazolidin-5-ones, having a potential synthetic and pharmacological value, there are only a few reports on their synthesis.1'2'3 In recent years conjugate addition of N-substituted hydroxylamines to a,S-unsaturated esters, followed by cyclization of the adduct to isoxazolidin-5-ones, has attracted attention of several laboratories.2'3"

📜 SIMILAR VOLUMES

Synthesis of enantiomerically pure (2R,
Synthesis of enantiomerically pure (2R, 5R) disubstituted pyrrolidines from D-mannitol
✍ M. Marzi; P. Minetti; D. Misiti 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 515 KB

Pyrrolidines 1 and 2 are obtained from D-Mannitol, giving good total yields and in an enantiomerically pure form. Some commentS and studies regarding pyrrolidine ring closure (key step) are also qorted. Over the last few years, interest in pyrrolidine-type derivatives has grown considerably, from b

Diastereoselective alkylation of 8-pheny
Diastereoselective alkylation of 8-phenylmenthyl 2-methylacetoacetate. Preparation of enantiomerically pure 4,4-disubstituted 2-pyrazolin-5-ones
✍ Marcial Moreno-Mañas; Rosa M. Sebastián; Adelina Vallribera; Elies Molins; Enriq 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 127 KB

Alkylation of (lR,3R,4S)-8-phenylmenthyl 2-methylacetoacetate with alkyl halides affords 2-alkyl-2-methylacetoacetates in diastereomeric ratios 72:28 to 85:15. The major R (at C-cx) diastereoisomers are converted into enantiopure 4,4-disubstituted 2pyrazolin-5-ones with recovery of the chiral induct