Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Title: Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Volume: 11 Issue: 1

Author(s): J. Holz, M.-N. Gensow, O. Zayas and A. Borner

Affiliation:

Keywords: diazabicyclooctane, lithium diisopropylamide, supercritical fluid chromatography, tetrahydropyran, p-toluenesulfonyl, middle pressure liquid chromatography

Abstract: The synthesis of chiral heterocyclic phosphines, such as phosphiranes, phosphetanes, phospholes and phosphinanes will be reviewed. These compounds play a pivotal role as ligands and organocatalysts, respectively, in asymmetric reactions. Synthetic approaches will be analyzed in the framework of several sub-categories e.g. the preparation of mono-, bis- and poly(phosphines). General synthetic strategies for the preparation of large families of related compounds will be considered such as 1.) stereoselective -alkylation of phosphine oxides or phosphine boranes, 2.) ring closure by substitution reactions and 3.) hydrogenations of unsaturated P-heterocylic compounds, followed by epimerization reactions. Besides these general methodologies also protocols leading to a single phosphine will be discussed. In some cases also the preparation of such phosphines will be presented, which have not yet been used in asymmetric catalysis, however, which have - owing to their structure - some relevance to synthetic methodologies or compounds discussed herein. For most phosphines presented applications in asymmetric catalytic reactions will be briefly mentioned together with characteristic enantioselectivities achieved.

Cite this article as:

Holz J., Gensow M.-N., Zayas O. and Borner A., Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis, Current Organic Chemistry 2007; 11 (1) . https://dx.doi.org/10.2174/138527207779316525