Stereospecific Cross-Coupling of α-(Thiocarbamoyl)organostannanes with Alkenyl, Aryl, and Heteroaryl Iodides
- 1 January 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (4) , 790-793
- https://doi.org/10.1021/ja064948q
Abstract
Racemic and scalemic PTC-protected α-hydroxystannanes cross-couple with alkenyl/aryl/heteroaryl iodides in moderate to good yields using copper(I) thiophene-2-carboxylate (CuTC) in THF at or below room temperature. Simple aryl iodides and 1-iodocyclohexene, two classes of electrophiles that typically react sluggishly, are also good substrates. Cross-couplings proceed with retention of configuration at the alkenyl- and stannyl-substituted stereocenters.Keywords
This publication has 19 references indexed in Scilit:
- Enantioselective Scandium-Catalyzed Vinylsilane Additions: A New Approach to the Synthesis of Enantiopure β,γ-Unsaturated α-Hydroxy Acid DerivativesJournal of the American Chemical Society, 2006
- Stereoselective Enzymatic Synthesis of Chiral Alcohols with the Use of a Carbonyl Reductase from Candida magnoliae with Anti-Prelog EnantioselectivityThe Journal of Organic Chemistry, 2006
- Concise Total Syntheses of Palominol, Dolabellatrienone, β-Araneosene, and Isoedunol via an Enantioselective Diels−Alder MacrobicyclizationJournal of the American Chemical Society, 2005
- Significant Enhancement of the Stille Reaction with a New Combination of Reagents—Copper(I) Iodide with Cesium FluorideChemistry – A European Journal, 2005
- Stille Coupling of Stereochemically Defined α-SulfonamidoorganostannanesJournal of the American Chemical Society, 2004
- Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilatorBioorganic & Medicinal Chemistry Letters, 2004
- Copper(II) Triflate-mediated Addition Reaction of α-Oxygenated Alkylstannanes to Imines for the Synthesis of vicinal-Amino Alcohol DerivativesChemistry Letters, 2003
- C-Glycosides: Pd/Cu Co-Catalyzed Thiocarboxylation of Stannyl GlucopyranosidesTetrahedron Letters, 1995
- Generation and electrophilic reactions of the 2,2,2-trifluoro-1-(phenylthio)ethyl carbocationThe Journal of Organic Chemistry, 1990
- Semibullvalenes. IV. 2,6- and 2,8-Trapping of the bicyclo[3.3.0]octadienyl diradical with oxygenJournal of the American Chemical Society, 1988