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.
| Original language | English |
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| Pages (from-to) | 9289-9291 |
| Number of pages | 3 |
| Journal | The Journal of Organic Chemistry |
| Volume | 69 |
| Issue number | 26 |
| Publication status | Published - 1 Jan 2004 |