Facile regio- and diastereoselective syntheses of hydroxylated 2-aminocyclohexanecarboxylic acids

F. Fülöp, Márta Palkó, E. Forró, Máté Dervarics, T. Martinek, Reijo Sillanpää

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

By means of total regio- and diastereoselective functionalizations of cis- and trans-2-amino-4-cyclohexenecarboxyric acid derivatives 1, 9, 12 and 16, isomers of 2-amino-4-hydroxycyclohexanecarboxylic acid 8 and 11, and 2-amino-5-hydroxycyclohexanecarboxylic acid 15 and 19 were prepared in good yields, via 1,3-oxazine or γ-lactone intermediates. The enantiomers of 8 and 15 were also prepared by the same pathway, resulting in products with ee > 99 %. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR, using some key vicinal couplings and characteristic NOEs.

Original languageEnglish
Pages (from-to)3214-3220
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number15
DOIs
Publication statusPublished - Jul 25 2005

Fingerprint

Oxazines
Stereochemistry
Acids
Enantiomers
Lactones
Isomers
Nuclear magnetic resonance
Derivatives
2-aminocyclohexanecarboxylic acid
4-hydroxycyclohexanecarboxylic acid
oxazine 1

Keywords

  • Amino acids
  • Diastereoselectivity
  • Heterocycles
  • Structure elucidation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Facile regio- and diastereoselective syntheses of hydroxylated 2-aminocyclohexanecarboxylic acids. / Fülöp, F.; Palkó, Márta; Forró, E.; Dervarics, Máté; Martinek, T.; Sillanpää, Reijo.

In: European Journal of Organic Chemistry, No. 15, 25.07.2005, p. 3214-3220.

Research output: Contribution to journalArticle

@article{ab2df175a3ab4b74a13f583962f6bef1,
title = "Facile regio- and diastereoselective syntheses of hydroxylated 2-aminocyclohexanecarboxylic acids",
abstract = "By means of total regio- and diastereoselective functionalizations of cis- and trans-2-amino-4-cyclohexenecarboxyric acid derivatives 1, 9, 12 and 16, isomers of 2-amino-4-hydroxycyclohexanecarboxylic acid 8 and 11, and 2-amino-5-hydroxycyclohexanecarboxylic acid 15 and 19 were prepared in good yields, via 1,3-oxazine or γ-lactone intermediates. The enantiomers of 8 and 15 were also prepared by the same pathway, resulting in products with ee > 99 {\%}. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR, using some key vicinal couplings and characteristic NOEs.",
keywords = "Amino acids, Diastereoselectivity, Heterocycles, Structure elucidation",
author = "F. F{\"u}l{\"o}p and M{\'a}rta Palk{\'o} and E. Forr{\'o} and M{\'a}t{\'e} Dervarics and T. Martinek and Reijo Sillanp{\"a}{\"a}",
year = "2005",
month = "7",
day = "25",
doi = "10.1002/ejoc.200500062",
language = "English",
pages = "3214--3220",
journal = "LIEBIGS ANN. CHEM.",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "15",

}

TY - JOUR

T1 - Facile regio- and diastereoselective syntheses of hydroxylated 2-aminocyclohexanecarboxylic acids

AU - Fülöp, F.

AU - Palkó, Márta

AU - Forró, E.

AU - Dervarics, Máté

AU - Martinek, T.

AU - Sillanpää, Reijo

PY - 2005/7/25

Y1 - 2005/7/25

N2 - By means of total regio- and diastereoselective functionalizations of cis- and trans-2-amino-4-cyclohexenecarboxyric acid derivatives 1, 9, 12 and 16, isomers of 2-amino-4-hydroxycyclohexanecarboxylic acid 8 and 11, and 2-amino-5-hydroxycyclohexanecarboxylic acid 15 and 19 were prepared in good yields, via 1,3-oxazine or γ-lactone intermediates. The enantiomers of 8 and 15 were also prepared by the same pathway, resulting in products with ee > 99 %. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR, using some key vicinal couplings and characteristic NOEs.

AB - By means of total regio- and diastereoselective functionalizations of cis- and trans-2-amino-4-cyclohexenecarboxyric acid derivatives 1, 9, 12 and 16, isomers of 2-amino-4-hydroxycyclohexanecarboxylic acid 8 and 11, and 2-amino-5-hydroxycyclohexanecarboxylic acid 15 and 19 were prepared in good yields, via 1,3-oxazine or γ-lactone intermediates. The enantiomers of 8 and 15 were also prepared by the same pathway, resulting in products with ee > 99 %. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR, using some key vicinal couplings and characteristic NOEs.

KW - Amino acids

KW - Diastereoselectivity

KW - Heterocycles

KW - Structure elucidation

UR - http://www.scopus.com/inward/record.url?scp=23044498527&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=23044498527&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200500062

DO - 10.1002/ejoc.200500062

M3 - Article

AN - SCOPUS:23044498527

SP - 3214

EP - 3220

JO - LIEBIGS ANN. CHEM.

JF - LIEBIGS ANN. CHEM.

SN - 1434-193X

IS - 15

ER -