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Molecules 2015, 20(4), 6153-6166; doi:10.3390/molecules20046153

Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones

Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK
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Author to whom correspondence should be addressed.
Academic Editor: John Spencer
Received: 10 March 2015 / Revised: 24 March 2015 / Accepted: 1 April 2015 / Published: 8 April 2015
(This article belongs to the Special Issue Recent Advances in Boron Chemistry)
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Abstract

The selective synthesis of 2,6-trans-tetrahydropyran derivatives employing the rhodium catalysed addition of organoboron reagents to dihydropyranone templates, derived from a zinc-catalysed hetero-Diels-Alder reaction, is reported. The addition of both arylboronic acids and potassium alkenyltrifluoroborates have been accomplished in high yields using commercially-available [Rh(cod)(OH)]2 catalyst. The selective formation of the 2,6-trans-tetrahydropyran stereoisomer is consistent with a mechanism involving alkene association and carbometalation on the less hindered face of the dihydropyranone. View Full-Text
Keywords: boronic acids; conjugate addition; rhodium; tetrahydropyran boronic acids; conjugate addition; rhodium; tetrahydropyran
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Edwards, H.J.; Goggins, S.; Frost, C.G. Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones. Molecules 2015, 20, 6153-6166.

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