Enantioselective synthesis of β-amino esters and its application to the synthesis of the enantiomers of the antidepressant Venlafaxine
- 14 June 2006
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 29,p. 3110-3112
- https://doi.org/10.1039/b605047f
Abstract
β-Amino esters are readily formed from the rhodium(II) prolinate-catalyzed intermolecular C–H insertion between methyl aryldiazoacetates and a bis-silyl protected methylamine.Keywords
This publication has 15 references indexed in Scilit:
- Double C−H Activation Strategy for the Asymmetric Synthesis of C2-Symmetric AnilinesOrganic Letters, 2004
- Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sitesBioorganic & Medicinal Chemistry Letters, 2004
- β2‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides1,2Peptide Science, 2004
- Catalytic Enantioselective C−H Activation by Means of Metal−Carbenoid-Induced C−H InsertionChemical Reviews, 2003
- New Strategic Reactions for Organic Synthesis: Catalytic Asymmetric C−H Activation α to Nitrogen as a Surrogate for the Mannich ReactionJournal of the American Chemical Society, 2003
- Catalytic Enantioselective Synthesis of β2-Amino Acids This work was supported by the National Science Foundation (CHE 0092490) and the National Institutes of Health (GM57425).Angewandte Chemie-International Edition, 2002
- Highly Regio-, Diastereo-, and Enantioselective C−H Insertions of Methyl Aryldiazoacetates into Cyclic N-Boc-Protected Amines. Asymmetric Synthesis of Novel C2-Symmetric Amines and threo-MethylphenidateJournal of the American Chemical Society, 1999
- Asymmetric synthesis of ß-amino acids and α-substituted β-amino acidsChemical Society Reviews, 1996
- 2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: synthesis and antidepressant activityJournal of Medicinal Chemistry, 1990
- Silicon in synthesis: stabase adducts - a new primary amine protecting group: alkylation of ethyl glycinateTetrahedron Letters, 1981