Inverse temperature dependence in the diastereoselective addition of Grignard reagents to a tetrahydrofurfural.
A remarkable example of inverse-temperature-dependent diastereoselectivity was uncovered while investigating the addition of Grignard reagents to a 3-hydroxytetrahydrofurfural. The free hydroxyl group in the tetrahydrofurfural was found to play a key role in these processes, a result corroborated through a series of DFT calculations that also highlighted an entropic preference for the formation of one diastereomer.
Mowat
Jeffrey
J
Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, Canada V5S 1S6.
Kang
Baldip
B
Fonovic
Branden
B
Dudding
Travis
T
Britton
Robert
R