A convenient synthesis of aziridine‐2‐carboxylic esters

Abstract

Optically active oxirane-2-carboxylic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide. The azido alcohols obtained were subsequently converted into aziridine-2-carboxylic esters by reaction with triphenylphosphine, in good yields and with high optical purity. Various racemic oxirane-2-carboxylic esters were subjected to the same sequence of reactions. Azidoh alcohols 6 Yield (%) 74 85 92 92 85 86 93 95 88 84 87 90 97 96 92 74 80 97 82 85 72 Johan Legters et al.

New Highly Efficient Stereoselective Synthesis of d-threo-PDMP

“…The morpholine residue was readily introduced via mesylate derivative 4, affording the epoxyamine 5 with an overall yield of 83% from 3. At this point, 5 was easily transformed in the corresponding aziridine amine 6 in the usual manner 11 and finally the reaction with di-tert-butyl dicarbonate gave 1 in satisfactory chemical yield.…”

Some Synthetic Uses of Double‐Bonded Functional Groups

“…These compounds (especially those with cis-stereochemistry) are especially useful for the synthesis of bioactive molecules 556 . There is thus significant effort in this area of synthesis 557,558 , but most methods are lengthy multistep procedures. Recently, a simple, one-pot procedure, utilizing imines, has been developed for the asymmetric synthesis of cis-N-substituted aziridine-2-carboxylic acids via a Darzens-type reaction (equation 154) 559 560 .…”

Studies on the Synthesis and Dynamic NMR Properties of 2-(Benzylidene amino)-N-[(R)-2-hydroxy-2-methyl-1-phenylpropyl]acetamide

“…These valuable threemembered heterocycles are available by enzymatic separation of the racemic mixtures [9], from ȕ-hydroxy Į-amino acids *Corresponding author. E-mail: m-chem41@guilan.ac.ir such as serine or threonine [10] or using oxiranes [11]. Furthermore, it can be obtained from Į,ȕ-unsaturated chiral imides relying on the reaction of 2,3-dihalocarboxylic acid derivatives with primary amines or ammonia [12], or from methods using chiral 3-benzoyloxyaminoimides [8a].…”