Title of article
Solvent effects on the diastereoselection in LiAlH4 reduction of α-substituted ketones
Author/Authors
Suzuki، نويسنده , , Yasumitsu and Kaneno، نويسنده , , Daisuke and Miura، نويسنده , , Masaya and Tomoda، نويسنده , , Shuji، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2008
Pages
4
From page
4223
To page
4226
Abstract
Based on high-level DFT calculations including solvent molecules, it was found that steric effects of solvent may be responsible for the diastereoselection in LiAlH4 reduction of acyclic ketones substituted by an oxygen-containing functional group at the α-position to the carbonyl. It was concluded that the conventional chelated transition state models lead to the predominance of the R∗,S∗-diastereoisomers against experimental observation.
Keywords
LiAlH4 reduction , diastereoselection , Solvent effect , Chelation model
Journal title
Tetrahedron Letters
Serial Year
2008
Journal title
Tetrahedron Letters
Record number
1859672
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