Copper-Catalyzed Aminohalogenation Using the 2-NsNCl2/2-NsNHNa Combination as the Nitrogen and Halogen Sources for the Synthesis of anti-Alkyl 3-Chloro-2-(o-nitrobenzenesulfonamido)-3-arylpropionates
- 27 June 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (15) , 2249-2252
- https://doi.org/10.1021/ol000120b
Abstract
New regio- and stereoselective aminohalogenation of cinnamic esters has been developed using the combination of 2-NsNCl(2)/2-NsNHNa as the nitrogen and chlorine sources and copper(I) triflate as the catalyst. The new procedure provides an efficient synthesis of anti-alkyl 3-chloro-2-(o-nitrobenzenesulfonamido)-3-phenylpropionate derivatives. Nine examples are presented with good yields (62-82%) and stereoselectivity ((5:1)-(30:1)).Keywords
This publication has 11 references indexed in Scilit:
- Enantioselective -Amino Acid Synthesis Based on Catalyzed Asymmetric Acyl Halide – Aldehyde Cyclocondensation ReactionsAngewandte Chemie International Edition in English, 2000
- Site-Selective N-Methylation of Peptides on Solid SupportJournal of the American Chemical Society, 1997
- Solid-Phase Synthesis of Peptide Mimetics with (E)-Alkene Amide Bond Replacements Derived from AlkenylaziridinesThe Journal of Organic Chemistry, 1997
- 2- and 4-Nitrobenzenesulfonamides: Exceptionally versatile means for preparation of secondary amines and protection of aminesTetrahedron Letters, 1995
- Total synthesis of allosamidin: an application of the sulfonamidoglycosylation of glycalsJournal of the American Chemical Society, 1991
- Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 9. New reagents for amination of the ethylenic linkageJournal of the Chemical Society, Perkin Transactions 1, 1978
- The chromous chloride promoted addition of N-haloamides to olefins. V. The addition of N-chloroamides to enol ethers: synthesis of acyloxy and acyl derivatives of α-amino acetals and ketals (aldehydes and ketones) and of 2-amino sugarsCanadian Journal of Chemistry, 1978
- The chromous chloride promoted addition of N-chlorocarbamates to enol ethers the synthesis of N-alkoxycarbonyl derivatives of 2-amino sugars and of α-amino ketones and aldehydesTetrahedron Letters, 1970
- Addition of N,N-dichlorosulfonamides to unsaturatesThe Journal of Organic Chemistry, 1968
- Addition of N,N-dichlorocarbamtes to conjugated dienesThe Journal of Organic Chemistry, 1968