Chiral induction from solvents-lactic acid esters in the asymmetric hydroboration of ketones

Stefan H. Hüttenhain*, Martin U. Schmidt, Fenja R. Schoepke, Magnus Rueping

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The hydroboration of acetophenone in the chiral solvent (S)-methyl lactate exhibits moderate enantioselectivities. A six-membered transition state involving the ketone, the borane, and the lactate as the only chiral source is proposed. Molecular modeling explains the experimentally observed enantioselectivities. Calculated ee-values are in accordance with those experimentally observed. Improved ee-values (up to 60%) can be obtained in the presence of stoichiometric amounts of Lewis acid at lower reaction temperatures.

Original languageEnglish (US)
Pages (from-to)12420-12423
Number of pages4
JournalTetrahedron
Volume62
Issue number52
DOIs
StatePublished - Dec 25 2006

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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