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Synthesis 2004(3): 326-328  
DOI: 10.1055/s-2004-815926
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Atropisomeric Biarylbisphosphines Derived from 2,2-Difluoro-1,3-benzo­dioxole

Frédéric Leroux, Joanna Gorecka, Manfred Schlosser*
Institut de Chimie moléculaire et biologique, Bâtiment de Chimie (BCh), Ecole polytechnique fédérale, 1015 Lausanne, Switzerland
Fax: +41(21)6939365; e-Mail: manfred.schlosser@epfl.ch;
Further Information

Publication History

Received 28 October 2003
Publication Date:
26 January 2004 (online)

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Abstract

Starting from the inexpensive 2,2-difluoro-1,3-benzodioxole or its 5-bromo derivative, two new atropisomeric bisphosphines have been prepared which, after racemate resolution, exhibit attractive features as ligands for enantioselective catalysts. The key step in their synthesis is a low temperature Ullmann reaction. An improved protocol secures coupling yields of 70-80%.

Key words

atropisomers - 2,2-difluoro-1,3-benzodioxole - bromo/lithium permutation - metalation - biarylbisphosphines

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