Electronic Tuning in C1-Symmetric Chelating Diphosphane Ligands Supported on Stereogenic Aryl-Heteroaryl Templates

Franco Sannicolò; Tiziana Benincori; Simona Rizzo; Serafino Gladiali; Sonia Pulacchini; Gianni Zotti

doi:10.1055/s-2001-18429

SPECIALTOPIC

Electronic Tuning in C ₁-Symmetric Chelating Diphosphane Ligands Supported on Stereogenic Aryl-Heteroaryl Templates

Franco Sannicolò*^a, Tiziana Benincori^b, Simona Rizzo^a, Serafino Gladiali*^c, Sonia Pulacchini^c, Gianni Zotti^d
^a Dipartimento di Chimica Organica e Industriale dell’Università e Centro CNR per la Sintesi e la Stereochimica di Speciali Sistemi Organici, Via Golgi 19, 20133 Milano, Italy
Fax: +39(02)58354139; e-Mail: staclaus@icil64.cilea.it;
^b Dipartimento di Scienze Chimiche, Fisiche e Matematiche dell’Università dell’Insubria, Via Valleggio 11, 22100 Como, Italy
^c Dipartimento di Chimica dell’Università, Via Vienna 2, 07100 Sassari, Italy
^d Istituto di Polarografia ed Elettrochimica Preparativa, C. N. R., c.so StatiUniti 4, 35020, Padova Italy

Abstract

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Abstract

The syntheses of a wide range of novel C ₁-symmetric chelating diphosphanes with stereogenic axes are reported. These ligands feature identical or different phosphanyl groups supported on diverse atropisomeric templates based on the interconnection of five-membered heteroaromatic and six-membered carbocyclic rings. Easy synthetic accessibility, independent tunability of the electronic and steric properties of the two phosphane donors, the low cost and the good stereoselection ability of some of them obtained in an enantiopure state are the main advantageous features of this class of ligands.

Key words

diphosphane ligands - heterocyclic diphosphanes - chiral ligands - C ₁ ligands - asymmetric hydrogenation

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Electronic Tuning in C 1-Symmetric Chelating Diphosphane Ligands Supported on Stereogenic Aryl-Heteroaryl Templates

Electronic Tuning in C ₁-Symmetric Chelating Diphosphane Ligands Supported on Stereogenic Aryl-Heteroaryl Templates