Asymmetric Ni(II)/Cr(II)-Mediated Coupling Reaction: Stoichiometric Process
- 9 November 2002
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (25) , 4431-4434
- https://doi.org/10.1021/ol0269805
Abstract
Via an X-ray analysis, the sulfonamide bearing R1 = i-Pr, R2 = Me, and R3 = Me is shown to be a tridentate ligand to a Cr(III) salt. This class of ligands, represented by R1 = t-Bu, R2 = 2-naphthyl, and R3 = Me, is effective to achieve an asymmetric Ni/Cr-mediated coupling reaction and, with the C14-C38 segment of halichondrins, its synthetic potential has been demonstrated. A possible mechanism is suggested for the process.Keywords
This publication has 19 references indexed in Scilit:
- Enantioselective Allylation of Aldehydes with (Dialkoxyallyl)chromium(III) ComplexesThe Journal of Organic Chemistry, 1997
- Ni(II)/Cr(II)-mediated coupling reaction: an asymmetric processThe Journal of Organic Chemistry, 1995
- Enantioselective Diels-Alder Reaction Using Chiral Lewis Acid Prepared from Grignard Reagent and a Chiral 2-(2-p-Toluenesulfonylamino)phenyl-4-phenyloxazolineTetrahedron Letters, 1995
- Total synthesis of halichondrin B and norhalichondrin BJournal of the American Chemical Society, 1992
- Antineoplastic agents. 219. Isolation and structure of the cell growth inhibitory constituents from the western Pacific marine sponge Axinella spJournal of Medicinal Chemistry, 1991
- Total synthesis of halichondrins: Highly stereoselective construction of a homochiral pentasubstituted H-ring pyran intermediate from α-d-glucoseTetrahedron Letters, 1989
- Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysisJournal of the American Chemical Society, 1986
- Catalytic effect of nickel(II) chloride and palladium(II) acetate on chromium(II)-mediated coupling reaction of iodo olefins with aldehydesJournal of the American Chemical Society, 1986
- Halichondrins - antitumor polyether macrolides from a marine spongePure and Applied Chemistry, 1986
- Norhalichondrin A: an antitumor polyether macrolide from a marine spongeJournal of the American Chemical Society, 1985