Diastereotopic Differentiation on Phosphorus Templates via the Ring-Closing Metathesis Reaction
- 12 May 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (12) , 1769-1772
- https://doi.org/10.1021/ol005952o
Abstract
A strategy is described in which the ring-closing metathesis reaction is utilized to desymmetrize a number of pseudo-C2-symmetric phosphorus templates 1−3. These reactions give excellent levels of selectivity (12−15:1) with vinyl phosphonamides containing a (E)-Ph group on the diastereotopic olefins. This approach is being developed as an effective method of obtaining P-chiral phosphonamides and phosphonates.Keywords
This publication has 15 references indexed in Scilit:
- A novel access to alicyclic phosphine oxides via ring closing metathesisTetrahedron Letters, 1999
- Diastereoselective Ring Closing Metathesis Reactions: Synthesis of Bicyclic Diallylic Alcohols and EthersAngewandte Chemie International Edition in English, 1999
- Ring closing metathesis reactions on a phosphonate templateTetrahedron Letters, 1998
- Phosphonate Diester and Phosphonamide Synthesis. Reaction Coordinate Analysis by 31P NMR Spectroscopy: Identification of Pyrophosphonate Anhydrides and Highly Reactive Phosphonylammonium Salts1Journal of the American Chemical Society, 1997
- Reductive Carbon–Sulfur Bond Cleavage: A Simple Pathway to Nonstabilized(Lithiomethyl)aminesAngewandte Chemie International Edition in English, 1996
- Asymmetric Ring-Closing Metathesis: Kinetic Resolution Catalyzed by a Chiral Molybdenum Alkylidene ComplexJournal of the American Chemical Society, 1996
- BIOLOGICAL ACTIVITY OF AMINOPHOSPHONIC ACIDSPhosphorus, Sulfur, and Silicon and the Related Elements, 1991
- A novel synthesis of metacyclophanes. Thermal and DDQ induced aromatization of bridgehead dienesJournal of the American Chemical Society, 1985
- Additions and Corrections - The Mechanism of the Dismutation of Superoxide Catalyzed by Copper(II) Phenanthroline Complex and of the Oxidation of Copper(I) Phenanthroline Complex by Oxygen in Aqueous SolutionJournal of the American Chemical Society, 1984
- Synthesis and characterization of a cyclic bimetallic complex of the trisulfide ionJournal of the American Chemical Society, 1981