Expedient Synthesis of Cyclopropane α-Amino Acids by the Catalytic Asymmetric Cyclopropanation of Alkenes Using Iodonium Ylides Derived from Methyl Nitroacetate
- 1 December 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (51) , 18014-18015
- https://doi.org/10.1021/ja056192l
Abstract
A highly enantioselective (up to 97.5% ee) and diastereoselective (95:5 dr trans/cis) Cu(I)-catalyzed cyclopropanation of alkenes using phenyliodonium ylide generated in situ from iodosobenzene and methyl nitroacetate is reported. The cyclopropanation took place with high enantioselectivity for a wide range of alkenes, and the reaction was performed at room temperature. 1-Nitrocyclopropyl esters are versatile building blocks to access the corresponding cyclopropane amino esters and aminocyclopropanes in two and three steps, respectively, from commercially available products.Keywords
This publication has 22 references indexed in Scilit:
- Synthesis of (1R,2S)-1-Amino-2-vinylcyclopropanecarboxylic Acid Vinyl-ACCA) Derivatives: Key Intermediates for the Preparation of Inhibitors of the Hepatitis C Virus NS3 ProteaseThe Journal of Organic Chemistry, 2005
- The Fourth Helical Secondary Structure of β‐Peptides: The (P)‐28‐Helix of a β‐Hexapeptide Consisting of (2R,3S)‐3‐Amino‐2‐hydroxy Acid ResiduesAngewandte Chemie International Edition in English, 2003
- Stereoselective Cyclopropanation ReactionsChemical Reviews, 2003
- Selective, High Affinity Peptide Antagonists of α-Melanotropin Action at Human Melanocortin Receptor 4: Their Synthesis and Biological Evaluation in VitroJournal of Medicinal Chemistry, 2001
- New Chiral Didehydroamino Acid Derivatives from a Cyclic Glycine Template with 3,6-Dihydro-2H-1,4-oxazin-2-one Structure: Applications to the Asymmetric Synthesis of Nonproteinogenic α-Amino AcidsThe Journal of Organic Chemistry, 2000
- Stereoselective synthesis of quaternary α-amino acids. Part 1: Acyclic compoundsTetrahedron: Asymmetry, 1998
- β-Turn Preferences Induced by 2,3-Methanophenylalanine ChiralityJournal of the American Chemical Society, 1998
- On the Conformational Bias of F((2R,3S)-cyclo-M)RFa Induced by thecis-2,3-Methanomethionine ResidueThe Journal of Organic Chemistry, 1996
- Structural determination of carnosadine, a new cyclopropyl amino acid, from red alga Grateloupia carnosaTetrahedron Letters, 1984
- The structure of coronatineJournal of the American Chemical Society, 1977