title: Al-isopropoxydiisobutylalane: a study of the effect of solvent on the rate and stereoselectivity of cyclic ketone reduction.
abstract: The effect of solvent on the rate and stereoselectivity of cyclic ketone reduction by Al-isopropoxydiisobutylalane (DIBA(i)OPr) has been investigated. In dichloromethane, DIBA(i)OPr behaves as a bulky reducing agent, approaching the carbonyl group along an equatorial trajectory to produce the axial alcohol with >10:1 stereoselectivity. In sharp contrast, reduction in toluene gives the complementary outcome, affording the thermodynamically more stable isomer with >99:1 stereoselectivity.
authors.affiliation: School of Chemistry, The University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.
authors.forename: Perdip S
authors.initials: PS
authors.lastname: Bahia
authors.forename: Matthew A
authors.initials: MA
authors.lastname: Jones
authors.forename: John S
authors.initials: JS
authors.lastname: Snaith