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Asymmetric synthesis of a chiral diarsine ligand via a cycloaddition reaction between 3,4-dimethyl-1-phenylarsole and diphenylvinylarsine.
- Source :
-
Tetrahedron: Asymmetry . Aug2014, Vol. 25 Issue 15, p1100-1103. 4p. - Publication Year :
- 2014
-
Abstract
- The organopalladium complex containing ortho-metallated (S)-[1-(dimethylamino)ethyl]naphthalene as a chiral auxiliary has been successfully employed to promote the asymmetric cycloaddition reaction between 3,4-dimethyl-1-phenylarsole and diphenylvinylarsine. In the intramolecular cycloaddition reaction, a pair of separable diastereomeric palladium complexes was obtained in the ratio of 6:1. The chiral naphthylamine auxiliary could be removed chemoselectively from the template by treatment with HCl and subsequently NaI to generate the neutral diiodo complex [(As-As)PdI2]. Treatment of the diiodo complex with KCN gave the enantiomerically pure As-As bidentate ligand in quantitative yield. In contrast to the reported similar P-P and As-P analogues, both arsenic donors in the diiodo complex could be readily eliminated to produce a structurally novel dimetallic complex. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 09574166
- Volume :
- 25
- Issue :
- 15
- Database :
- Academic Search Index
- Journal :
- Tetrahedron: Asymmetry
- Publication Type :
- Academic Journal
- Accession number :
- 97542713
- Full Text :
- https://doi.org/10.1016/j.tetasy.2014.06.005