Stereocontrolled synthesis of cyclopropanol amino acids from allylic sulfones: conformationally restricted building blocks

David Díez; P Garcia; Isidro S Marcos; N M Garrido; P Basabe; Howard B Broughton; Julio G Urones

doi:10.1021/ol035451d

Stereocontrolled synthesis of cyclopropanol amino acids from allylic sulfones: conformationally restricted building blocks

Org Lett. 2003 Oct 2;5(20):3687-90. doi: 10.1021/ol035451d.

Authors

David Díez¹, P Garcia, Isidro S Marcos, N M Garrido, P Basabe, Howard B Broughton, Julio G Urones

Affiliation

¹ Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain.

PMID: 14507205
DOI: 10.1021/ol035451d

Abstract

[reaction: see text] A new amino acid methyl ester with a cyclopropanol has been synthesized starting from the allyl sulfone 10. The starting material, 10, could be obtained in both enantiomeric forms. The stereoselectivity of the cyclopropane formation has been studied by molecular modeling.

Publication types

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

MeSH terms

Allyl Compounds / chemistry*
Amino Acids / chemical synthesis*
Amino Acids / chemistry
Crystallography, X-Ray
Cyclization
Ethers, Cyclic / chemistry*
Glutamic Acid / chemistry
Models, Molecular
Molecular Conformation
Molecular Structure
Stereoisomerism
Sulfones / chemistry*

Substances

Allyl Compounds
Amino Acids
Ethers, Cyclic
Sulfones
cyclopropanol
Glutamic Acid