63364-60-3

Upstream product

• 97935-34-7 Potassium; (1R,2S)-2-ethyl-1-methoxycarbonyl-cyclopropanecarboxylate 
• 18795-92-1 1,1-dimethyl 2-ethylcyclopropane-1,1-dicarboxylate 
• 138457-95-1 (1S,2S)-1-Amino-2-ethyl-cyclopropanecarboxylic acid methyl ester 
• 87429-76-3 1-Azido-2-ethyl-cyclopropanecarboxylic acid 
• 97935-31-4 2-ethylcyclopropane-1,1-dicarboxylic acid di-tert-butyl ester 
• 88950-66-7 (1RS,2SR)-1-[(tert-butoxycarbonyl)amino]-2-ethylcyclopropane-1-carboxylic acid 
• 134639-29-5 C₁₆H₂₃NO₂ 
• 87429-74-1 3-Azido-4-ethyl-4,5-dihydro-3H-pyrazole-3-carboxylic acid methyl ester 
• 81852-62-2 Methyl (Z)-2-azido-pentenoate 

Downstream Products

• 98244-40-7 (1S,2R)-1-((S)-2-Ethoxycarbonyloxy-2-phenyl-acetylamino)-2-ethyl-cyclopropanecarboxylic acid methyl ester 
• 98244-44-1 (1S,2R)-1-((R)-2-Ethoxycarbonyloxy-2-phenyl-acetylamino)-2-ethyl-cyclopropanecarboxylic acid methyl ester 
• 98189-21-0 (1R,2S)-1-((S)-2-Ethoxycarbonyloxy-2-phenyl-acetylamino)-2-ethyl-cyclopropanecarboxylic acid methyl ester 
• 65878-52-6 (+)-(1S,2R)-allocoronamic acid 
• 65878-53-7 (+)-(1R,2S)-allocoronamic acid 
• 106-98-9 1-butylene 

Relevant academic research and scientific papers

A CONVENIENT SYNTHESIS OF REGIO-SPECIFICALLY 2-ALKYLATED-3-DEUTERIATED-1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACIDS

A simple procedure for the large scale preparations of regio-specifically 2-alkylated-3-deuteriated-1-aminocyclopropane-1-carboxylic acids from 1-deuterio-1,2-dibromoalkanes is described.

Titanium-mediated diastereoselective formation of (E)- or (Z)-2-substituted 1-vinylcyclopropanols: Scope and limitation, applications

Titanium-mediated cyclopropanation of α,β-unsaturated esters failed to provide 1-vinylcyclopropanol derivatives in useful yields, but (E)-2-substituted-1-vinylcyclopropanols were formed diastereoselectively from O-protected β-oxo- and β-halo esters, with the allylic double bond being created subsequently (Knoevenagel condensation or dehydrohalogenation). Titanium-mediated cyclopropanation of homoallyl alk-2-enoates, on the other hand, directly provided the corresponding Z diastereomers. Palladium(0)-catalysed azidation of their sulfonic esters (tosylate, mesylate), azide reduction, and subsequent double bond cleavage afforded (E)- or (Z)-2-alkyl-2,3-methanoamino acids, although improvements are required to perform the total asymmetric syntheses of molecules with three membered-rings by these methods. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: A new preparation of 2,3-methanoamino acids

The diastereoselective titanium(IV)-mediated cyclopropanation of ethyl 3,3-diethoxypropionate by Grignard reagents, followed by modified Knoevenagel condensation with malonic acid under microwave irradiation, allow the preparation of (E)-1-(1-alkenyl)cyclopropanol derivatives, suitable precursors of πn-1,1-dimethyleneallylmetal species. The azidation of such complexes, followed by a reduction-oxidation sequence led to pure (E)-2,3-methanoamino acids. (C) 2000 Elsevier Science Ltd.

Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids

One-pot palladium(0)-catalyzed alkylation and S(N') cyclization of 1,4- dichlorobut-2-ene 1 by the anion of α-substituted carbonitriles 2a-d can provide highly functionalized cyclopropanes (E)-4a-d, diastereoselectivity, (de 88-100%). Several attempts to achieve the asymmetric synthesis of the 1- amino-2-ethenylcyclopropanecarbonitrile (E)-9, by means of this new procedure, i.e., using chiral palladium ligands, chiral aminoacetonitriles (- )- and (+)-12 (from 1-hydroxypinanone) or chiral allyl chlorides (4S)-20b-d and (4R)-20e (from (2S) ethyl lactate) have pointed up the reversibility of the palladium-catalyzed cyclization step, responsible for the low enantioselectivity observed (ee ≤ 32%) and for the formation of byproducts, i.e., azepine derivatives 8a,b arising from subsequent aza Cope ring expansion. Molecular mechanics calculations using a modified MM2 type force field adapted to the π-allyl palladium complexes have explained these results. However, When performed under the Mitsunobu reaction conditions (DEAD, PMe3), therefore, in the absence of palladium catalyst, the S(N'), cyclization occurred also diastereoselectively (de > 88%) and provided the enantiomerically enriched 1-amino-2-propenylcyclopropanecarbonitrile (E)-22 (ee > 83%) suitable precursor of (1S,2S)-2,3-methanoamino acids.

ASYMMETRIC SYNTHESIS OF CIS AND TRANS 2-METHYL AND 2-ETHYL 1-AMINO CYCLOPROPANECARBOXYLIC ACIDS

A new four step asymmetric synthesis of 2-methyl and 2-ethyl 1-amino cyclopropane carboxylic acids resulted from the cycloaddition of diazomethane to the corresponding chirally derivatized dehydro-aminoacid.

SYNTHESIS OF 1-AZIDOCYCLOPROPANECARBOXYLATES FROM 2-AZIDO-2-ALKENOATES

Addition of diazomethane to 2-azido-2-alkenoates followed by pyrolysis of the resulting pyrazoline derivatives affords the title compounds.