TY - JOUR
T1 - Trans-selective rhodium catalysed conjugate addition of organoboron reagents to dihydropyranones
AU - Edwards, Hannah J.
AU - Goggins, Sean
AU - Frost, Christopher G.
PY - 2015/4
Y1 - 2015/4
N2 - 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.
AB - 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.
KW - Boronic acids
KW - Conjugate addition
KW - Rhodium
KW - Tetrahydropyran
UR - http://www.scopus.com/inward/record.url?scp=84928725225&partnerID=8YFLogxK
UR - http://dx.doi.org/10.3390/molecules20046153
UR - http://www.mdpi.com/1420-3049/20/4/6153
U2 - 10.3390/molecules20046153
DO - 10.3390/molecules20046153
M3 - Article
AN - SCOPUS:84928725225
SN - 1420-3049
VL - 20
SP - 6153
EP - 6166
JO - Molecules
JF - Molecules
IS - 4
ER -