Three-component Synthesis of Alpha,beta-cyclopropyl-gamma-amino Acids

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2005 Mar 12

PMID 15760158

Citations 8

Authors

Peter Wipf

Corey R J Stephenson

Affiliations

Soon will be listed here.

Abstract

[reaction: see text] The multicomponent coupling of alkenylzirconocenes with N-diphenylphosphinoyl imines provides rapid access to functionalized C-cyclopropylalkylamides which have been readily transformed into alpha,beta-cyclopropyl-gamma-amino acids. These novel scaffolds are thus accessible in ca. 8 steps from commercially available alkynes.

Citing Articles

Ethyl dibromofluoroacetate: a versatile reagent for the synthesis of fluorinated molecules.

David E, Couve-Bonnaire S, Jubault P, Pannecoucke X Tetrahedron. 2020; 69(52):11039-11055.

PMID: 32287427 PMC: 7126840. DOI: 10.1016/j.tet.2013.10.048.

A practical method for N-alkylation of phosphinic (thio)amides with alcohols via transfer hydrogenation.

Jankins T, Qin Z, Engle K Tetrahedron. 2019; 75(24):3272-3281.

PMID: 31745374 PMC: 6863173. DOI: 10.1016/j.tet.2019.04.029.

Large-scale asymmetric synthesis of the bioprotective agent JP4-039 and analogs.

Frantz M, Pierce J, Pierce J, Kangying L, Qingwei W, Johnson M Org Lett. 2011; 13(9):2318-21.

PMID: 21452836 PMC: 3089766. DOI: 10.1021/ol200567p.

Enantioselective synthesis of homoallylic amines through reactions of (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkene-substituted aldimines catalyzed by chiral C1-symmetric NHC-Cu complexes.

Vieira E, Snapper M, Hoveyda A J Am Chem Soc. 2011; 133(10):3332-5.

PMID: 21341657 PMC: 3059089. DOI: 10.1021/ja200311n.

Peptide-Like Molecules (PLMs): A Journey from Peptide Bond Isosteres to Gramicidin S Mimetics and Mitochondrial Targeting Agents.

Wipf P, Xiao J, Stephenson C Chimia (Aarau). 2010; 63(11):764-775.

PMID: 20725595 PMC: 2922051. DOI: 10.2533/chimia.2009.764.