Asymmetric Wolff Rearrangement Reactions with α-Alkylated-α-diazoketones: Stereoselective Synthesis of α-Substituted-β-amino Acid Derivatives
- 17 June 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (14), 2177-2179
- https://doi.org/10.1021/ol006146k
Abstract
Photoinduced asymmetric Wolff rearrangement reactions were performed with α-amino-α‘-methyl-α‘-diazoketones to afford α-methyl-β-amino acid esters with good stereoselectivity. Factors that may influence the stereochemistry were examined, including steric effects and temperature dependence, which had a great impact on the stereochemistry.Keywords
This publication has 7 references indexed in Scilit:
- Amination of Ketene: A Theoretical StudyJournal of the American Chemical Society, 1998
- Recent stereoselective synthetic approaches to β-amino acidsTetrahedron, 1994
- β-Oxy-α-diazo carbonyl compounds. I. Photochemistry of chiral β-oxy-α-diazo methyl ketones. Stereoselective synthesis of chiral macrolide synthons.Tetrahedron Letters, 1993
- .alpha.-Hydroxy esters as chiral reagents: asymmetric synthesis of 2-arylpropionic acidsJournal of the American Chemical Society, 1989
- Umlagerungsreaktionen, V. Eine kinetische Studie zum Mechanismus der Wolff‐UmlagerungEuropean Journal of Inorganic Chemistry, 1970
- The Structure of Diazoketones. A Study of Hindered Internal Rotation1,2Journal of the American Chemical Society, 1966
- New Reactions on Decomposition of a Hindered α-Diazoketone1The Journal of Organic Chemistry, 1959