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Issue 5, 2016
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P-chiral 1-phosphanorbornenes: from asymmetric phospha-Diels–Alder reactions towards ligand design and functionalisation

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Abstract

The principle of stereotopic face differentiation was successfully applied to 2H-phospholes which undergo a very efficient and highly stereoselective Diels–Alder reaction giving phosphorus-chiral 1-phosphanorbornenes with up to 87% yield. The observed reaction pathway has been supported by theoretical calculations showing that the cycloaddition reaction between 2H-phosphole 3a and the dienophile (5R)-(−)-menthyloxy-2(5H)-furanone (8) is of normal electron demand. Optically pure phosphanes were obtained by separation of the single diastereomers and subsequent desulfurisation of the sulfur-protected phosphorus atom. Finally, divergent ligand synthesis is feasible by reduction of the chiral auxiliary, subsequent stereospecific intramolecular Michael addition, and various functionalisations of the obtained key compound 13a. Furthermore, the unique structural properties of phospanorbornenes are presented and compared to those of phosphanorbornanes.

Graphical abstract: P-chiral 1-phosphanorbornenes: from asymmetric phospha-Diels–Alder reactions towards ligand design and functionalisation

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Supplementary files

Article information


Submitted
07 Jul 2015
Accepted
30 Jul 2015
First published
30 Jul 2015

This article is Open Access

Dalton Trans., 2016,45, 1904-1917
Article type
Paper

P-chiral 1-phosphanorbornenes: from asymmetric phospha-Diels–Alder reactions towards ligand design and functionalisation

T. Möller, P. Wonneberger, M. B. Sárosi, P. Coburger and E. Hey-Hawkins, Dalton Trans., 2016, 45, 1904
DOI: 10.1039/C5DT02564H

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