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Synthesis 2015; 47(10): 1461-1468
DOI: 10.1055/s-0034-1380407
paper
© Georg Thieme Verlag Stuttgart · New York

Highly Diastereoselective Cobalt-Mediated C(sp3)–C(sp2) Cross-Coupling Reactions of Cyclic Halohydrins with (Hetero)Aryl Grignard Reagents

Jeffrey M. Hammann
Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 Munich, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Diana Haas
Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 Munich, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Andreas K. Steib
Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 Munich, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Paul Knochel*
Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 Munich, Germany   Email: paul.knochel@cup.uni-muenchen.de
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Further Information

Publication History

Received: 23 January 2015

Accepted after revision: 28 January 2015

Publication Date:
03 March 2015 (online)

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Abstract

The highly diastereoselective cobalt-mediated cross-coupling of cyclic tert-butyldimethylsilyl-protected iodohydrins or bromohydrins with (hetero)arylmagnesium reagents has been expanded further. The method can be applied to a broad range of electron-poor and electron-rich Grignard reagents, furnishing the respective functionalized trans-2-arylcycloalcohols with diastereomeric ratios up to 99:1.

Key words

cobalt - diastereoselectivity - cross-coupling - Grignard reagents - arenes

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034–1380407.
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