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

Molecules

Hannah J. Edwards²  Sean Goggins²  Christopher G. Frost¹ 

[1] Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK;

关键词: boronic acids;    conjugate addition;    rhodium;    tetrahydropyran;   

DOI  :  10.3390/molecules20046153

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.