(2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates

A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate (( Z)- 6, ( E)- 6) was obtained by thermally induced cyclopropanation of α-methylacrolein with α-diazobenzylphosphonate 5. Application of proline or proline-derived organocatalysts accelerated the reaction, but h...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2011-04, Vol.67 (16), p.2849-2857
Main Authors: El-Gokha, Ahmed, Maas, Gerhard
Format: Article
Language:English
Subjects:
(Aminoalkyl)phosphonates
Acceptor-substituted cyclopropanes
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Amino acids
Catalysis
Catalysts: preparations and properties
Chemistry
Cyclopropylphosphonates
Dimethyl
Esters
Exact sciences and technology
General and physical chemistry
Glycine
Organic chemistry
Organocatalysis
Preparations and properties
Proline
Reduction
Tetrahedrons
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate (( Z)- 6, ( E)- 6) was obtained by thermally induced cyclopropanation of α-methylacrolein with α-diazobenzylphosphonate 5. Application of proline or proline-derived organocatalysts accelerated the reaction, but had a minor effect on the Z/ E ratio of 6. By reaction with benzylamine or methyl esters of glycine, ( S)-alanine, and ( S)-phenylalanine, the Z/ E-mixture of 6 was converted into cyclopropylaldimines, which after reduction gave the corresponding N-substituted (2-aminomethyl-cyclopropyl)phosphonates. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.02.068