Stereoselectivity in the Reduction of Aliphatic α-Ketols with Aluminum Hydride Reagents

John A. Katzenellenbogen, Stephen B. Bowlus

Research output: Contribution to journalArticlepeer-review

Abstract

The reduction of six α-ketols with different patterns of substitution and size of substituents has been investigated using seven aluminum hydride reagents. The ratio of diastereomeric diols produced was determined by 220-MHz nmr analysis. In each case the predominant diol was the one predicted by Cram's cyclic model. The degree of stereoselectivity correlates well with α-ketol structure with only one reagent (triisobutylaluminum). With the other (agglomerated) reagents, selectivity is related only in an irregular manner to α-ketol structure.

Original languageEnglish (US)
Pages (from-to)627-632
Number of pages6
JournalJournal of Organic Chemistry
Volume38
Issue number4
DOIs
StatePublished - Feb 1 1973

ASJC Scopus subject areas

  • Organic Chemistry

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