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Open AccessArticle

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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Academic Editor: John Spencer
Molecules 2015, 20(4), 6153-6166; https://doi.org/10.3390/molecules20046153
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)
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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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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