Diastereoselection in the LiA1H4 reduction of severely hindered β-diketones examples of anti-curtin-hammett preequilibrium conditions

Marcial Moreno-Mañas, Nicanor Galvez, Maria E. Lloris, Jorge Marquet, Antonio C. Siani

Research output: Contribution to journalArticleResearchpeer-review

4 Citations (Scopus)

Abstract

LiA1H4 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 (2R,3r,4S) meso diol. © 1992.
Original languageEnglish
Pages (from-to)3603-3610
JournalTetrahedron
Volume48
Issue number17
DOIs
Publication statusPublished - 1 Jan 1992

Keywords

  • Curtin-Hammett Principle
  • Diastereoselectivity
  • Reduction of β-diketones

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