Stereocontrolled synthesis of five diastereomers of trimethyl 3-aminocyclopentane-1,2,4-tricarboxylates

Ferenc Miklós, I. Mándity, Reijo Sillanpää, F. Fülöp

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The sterically controlled oxidative cleavage of N-protected diexo- and diendo-substituted norbornene β-amino acids/esters resulted in four trimethyl 3-aminocyclopentane-1,2,4-carboxylate diastereomers. The sodium methoxide mediated isomerization of the four diastereomers in all cases yielded the thermodynamically most stable all-trans stereoisomer as a single product.

Original languageEnglish
Pages (from-to)3769-3772
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number29
DOIs
Publication statusPublished - Jul 17 2013

Fingerprint

Stereoisomerism
Isomerization
Methanol
Esters
Amino Acids
2-norbornene

Keywords

  • β-Aminotricarboxylic acid
  • Epimerization
  • Isomerization
  • Oxidative cleavage
  • Potassium permanganate oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereocontrolled synthesis of five diastereomers of trimethyl 3-aminocyclopentane-1,2,4-tricarboxylates. / Miklós, Ferenc; Mándity, I.; Sillanpää, Reijo; Fülöp, F.

In: Tetrahedron Letters, Vol. 54, No. 29, 17.07.2013, p. 3769-3772.

Research output: Contribution to journalArticle

@article{597aea631f8247ef894d63d5c8fe17ad,
title = "Stereocontrolled synthesis of five diastereomers of trimethyl 3-aminocyclopentane-1,2,4-tricarboxylates",
abstract = "The sterically controlled oxidative cleavage of N-protected diexo- and diendo-substituted norbornene β-amino acids/esters resulted in four trimethyl 3-aminocyclopentane-1,2,4-carboxylate diastereomers. The sodium methoxide mediated isomerization of the four diastereomers in all cases yielded the thermodynamically most stable all-trans stereoisomer as a single product.",
keywords = "β-Aminotricarboxylic acid, Epimerization, Isomerization, Oxidative cleavage, Potassium permanganate oxidation",
author = "Ferenc Mikl{\'o}s and I. M{\'a}ndity and Reijo Sillanp{\"a}{\"a} and F. F{\"u}l{\"o}p",
year = "2013",
month = "7",
day = "17",
doi = "10.1016/j.tetlet.2013.05.009",
language = "English",
volume = "54",
pages = "3769--3772",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "29",

}

TY - JOUR

T1 - Stereocontrolled synthesis of five diastereomers of trimethyl 3-aminocyclopentane-1,2,4-tricarboxylates

AU - Miklós, Ferenc

AU - Mándity, I.

AU - Sillanpää, Reijo

AU - Fülöp, F.

PY - 2013/7/17

Y1 - 2013/7/17

N2 - The sterically controlled oxidative cleavage of N-protected diexo- and diendo-substituted norbornene β-amino acids/esters resulted in four trimethyl 3-aminocyclopentane-1,2,4-carboxylate diastereomers. The sodium methoxide mediated isomerization of the four diastereomers in all cases yielded the thermodynamically most stable all-trans stereoisomer as a single product.

AB - The sterically controlled oxidative cleavage of N-protected diexo- and diendo-substituted norbornene β-amino acids/esters resulted in four trimethyl 3-aminocyclopentane-1,2,4-carboxylate diastereomers. The sodium methoxide mediated isomerization of the four diastereomers in all cases yielded the thermodynamically most stable all-trans stereoisomer as a single product.

KW - β-Aminotricarboxylic acid

KW - Epimerization

KW - Isomerization

KW - Oxidative cleavage

KW - Potassium permanganate oxidation

UR - http://www.scopus.com/inward/record.url?scp=84879014338&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84879014338&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.05.009

DO - 10.1016/j.tetlet.2013.05.009

M3 - Article

AN - SCOPUS:84879014338

VL - 54

SP - 3769

EP - 3772

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 29

ER -