Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to DihydropyranonesReport as inadecuate




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Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK





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Academic Editor: John Spencer

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 RhcodOH2 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





Author: Hannah J. Edwards, Sean Goggins and Christopher G. Frost *

Source: http://mdpi.com/



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