The Journal of organic chemistry

Al-isopropoxydiisobutylalane: A study of the effect of solvent on the rate and stereoselectivity of cyclic ketone reduction

PS Bahia, MA Jones, JS Snaith

Index: Bahia, Perdip S.; Jones, Matthew A.; Snaith, John S. Journal of Organic Chemistry, 2004 , vol. 69, # 26 p. 9289 - 9291

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Citation Number: 15

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 ...

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