𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Preparation of bicyclic boroxazolidones from aziridine-2-carboxylic esters

✍ Scribed by Johan Legters; Lambertus Thijs; Binne Zwanenburg

Book ID
104589412
Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
367 KB
Volume
111
Category
Article
ISSN
0165-0513

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Aziridine‐2‐carboxylic esters 1 were converted into bicyclic boroxazolidones 3 in a three‐step sequence. First, the ester groups were hydrolyzed either by sodium hydroxide or with lithium hydroxide in methanol. The salts thus obtained were acidified with acetic acid or through a weakly acidic ion‐exchange resin. Treatment of the zwitterionic aziridine‐2‐carboxylic acids 2 with triethyl‐borane in hexane gave boroxazolidones 3 in high yields. Boroxazolidone 3g, obtained from optically active 1g was reconverted to the starting material by 8‐hydroxyquinoline without any loss of optical activity.

📜 SIMILAR VOLUMES

Conversion of aziridine-2-carboxylic est
Conversion of aziridine-2-carboxylic esters into 2H-azirine-2-carboxylic esters
✍ Johan Legters; Lambertus Thijs; Binne Zwanenburg 📂 Article 📅 2010 🏛 Elsevier Science 🌐 English ⚖ 371 KB

## Abstract Aziridine‐2‐carboxylic esters 1 were converted into 2__H__‐azirine‐2‐carboxylic esters 4 in two steps. Treatment of 1 with __tert__‐butyl hypochlorite in ether gave smooth __N__‐chlorination. Reaction of __N__‐chloroaziridines 2 with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) or 1,4‐diaza

Esters and amides from aziridine 2-carbo
Esters and amides from aziridine 2-carboxylic acid salts
✍ C. Lambert; H.G. Viehe 📂 Article 📅 1985 🏛 Elsevier Science 🌐 French ⚖ 188 KB

## Potassiiim salts of azlridlne-A 7-carboxylic acid derivatives are efficiently converted into esters of amides by reactions with alkyl halides, alkyl ditwliJL*s or by acyiatiorl with trimethylacetyl chloride followed by aminolys*s. Azlrjdlnc be,r,gs to a class of alkylatlng compounds of Importan

Easy access to β-halo amino esters and a
Easy access to β-halo amino esters and aziridine 2-carboxylic esters from halohydrins
✍ Saı̈d Boukhris; Abdelaziz Souizi 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 96 KB

The halohydrins prepared from epoxide esters, were treated with hydroxylamine derivatives. In subsequent reaction with NaOH/K 2 CO 3 /Bu 4 NHSO 4 the N-protected b-halo a-aminoesters thus obtained were converted into N-hydroxy ariridine 2-carboxylic esters in good yields.