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Diastereoselection in the LiA1H4reduction of severely hindered β-diketones examples ofanti-curtin-hammett preequilibrium conditions

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
48
Issue
17
Identifiers
DOI: 10.1016/s0040-4020(01)88498-2
Keywords
  • Reduction Of β-Diketones
  • Diastereoselectivity
  • Curtin-Hammett Principle

Abstract

Abstract LiA1H 4 Reduction of α-adamantyl(and tert -butyl)-β-diketones occur under anti -Curtin-Hammett preequilibrium conditions, each preferred conformer leading to a different stereoisomeric diol, whereas reduction of 3-adamantyl-3-methyl(and ethyl)pentane-2-,4-dione occurs with high diastereoselectivity to afford only the (2 R ,3 r ,4 S ) meso diol.

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