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Literature DB >> 15760158

Three-component synthesis of alpha,beta-cyclopropyl-gamma-amino acids.

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.

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 15760158 DOI： 10.1021/ol0501525

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

8 in total

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

Authors: Peter Wipf; Jingbo Xiao; Corey R J Stephenson
Journal: Chimia (Aarau) Date: 2009-11 Impact factor: 1.509

2. 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.

Authors: Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2011-02-22 Impact factor: 15.419

Three-component synthesis of alpha,beta-cyclopropyl-gamma-amino acids.

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

2. 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.

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

4. An asymmetric total synthesis of brevisamide.

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

6. Triple hybrids of steroids, spiroketals, and oligopeptides as new biomolecular chimeras.

7. Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines.

Review 8. Ethyl dibromofluoroacetate: a versatile reagent for the synthesis of fluorinated molecules.