Enantioselective synthesis of fluorinated alpha-amino acids and derivatives in combination with ring-closing metathesis: intramolecular pi-stacking interactions as a source of stereocontrol

S Fustero; A Navarro; B Pina; J G Soler; A Bartolomé; A Asensio; A Simón; P Bravo; G Fronza; A Volonterio; M Zanda

doi:10.1021/ol016087q

Enantioselective synthesis of fluorinated alpha-amino acids and derivatives in combination with ring-closing metathesis: intramolecular pi-stacking interactions as a source of stereocontrol

Org Lett. 2001 Aug 23;3(17):2621-4. doi: 10.1021/ol016087q.

Authors

S Fustero¹, A Navarro, B Pina, J G Soler, A Bartolomé, A Asensio, A Simón, P Bravo, G Fronza, A Volonterio, M Zanda

Affiliation

¹ Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, E-46100 Burjassot, Valencia, Spain. santos.fustero@uv.es

PMID: 11506593
DOI: 10.1021/ol016087q

Abstract

[reaction: see text]. Hydride reduction of C=N bonds stereocontrolled by intramolecular pi-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta-amino alcohols and alpha-amino acid derivatives, respectively.

Publication types

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

MeSH terms

Amino Acids / chemical synthesis*
Amino Acids / chemistry
Fluorine / chemistry*
Molecular Structure
Stereoisomerism

Substances

Amino Acids
Fluorine