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Synthesis of cyclopropanes via organoiron methodology: preparation of 2-(2′-carboxy-3′-ethylcyclopropyl)glycine

✍ Scribed by Kamil Godula; William A Donaldson

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
55 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

A route to 1,2,3-trisubstituted cyclopropanes has been developed. The relative stereochemistry at the three cyclopropane centers is established by nucleophilic attack on the pentadienyl ligand on the face opposite to iron and subsequent oxidatively induced reductive elimination with retention of configuration. This methodology was applied to the synthesis of 2-(2%-carboxy-3%-ethylcyclopropyl)glycines. The diastereomeric glycine dimethyl esters are separable as their diphenylmethylene imines.

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Synthesis of cyclopropanes via organoiro
Synthesis of cyclopropanes via organoiron methodology: stereoselective preparation of cis-2-(2′-carboxycyclopropyl)glycine
✍ Nathaniel J Wallock; William A Donaldson 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 80 KB

A stereoselective route to cis-2-(2%-carboxycyclopropyl)glycine has been developed. exo-Nucleophilic addition to the (bicyclo[5.1.0]octadienyl)iron(1+) cation establishes the relative stereochemistry at the cyclopropane ring and the a-stereocenter. Subsequent removal of the metal and cleavage of the