New 1,3-amino alcohols derived from enantiopure bridgehead β-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acids

Christophe André; Monique Calmès; Françoise Escale; Muriel Amblard; Jean Martinez; Olivier Songis

doi:10.1007/s00726-011-1097-6

New 1,3-amino alcohols derived from enantiopure bridgehead β-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acids

Amino Acids. 2012 Jul;43(1):415-21. doi: 10.1007/s00726-011-1097-6. Epub 2011 Oct 4.

Authors

Christophe André¹, Monique Calmès, Françoise Escale, Muriel Amblard, Jean Martinez, Olivier Songis

Affiliation

¹ Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS-Université Montpellier 1 et 2, Bâtiment Chimie (17), Université Montpellier 2, place E. Bataillon, 34095, Montpellier Cedex 5, France.

PMID: 21968501
DOI: 10.1007/s00726-011-1097-6

Abstract

Constrained enantiopure bicyclic β-amino acids derived from the asymmetric Diels-Alder reaction of the (R)-benzyl-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)-benzoate and the 1-(benzyloxycarbonylamino)cyclohexadiene provide original templates for the construction of new rigid enantiopure 1,3-amino alcohols.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry*
Amino Alcohols / chemical synthesis*
Amino Alcohols / chemistry
Bridged Bicyclo Compounds / chemistry*
Carboxylic Acids / chemistry
Molecular Structure
Stereoisomerism

Substances

Amino Acids
Amino Alcohols
Bridged Bicyclo Compounds
Carboxylic Acids