Chiral trialkylborane reducing agents. Preparation of 1-deuterio primary alcohols of high enantiomeric purity

M. Mark Midland, Sue Greer, Alfonso Tramontano, Stephen A. Zderic

Research output: Contribution to journalArticle

175 Scopus citations

Abstract

B-3-Pinanyl-9-borabicyclo[3.3.1]nonane (3-pinanyl-9-BBN, prepared from (+)-α-pinene and 9-BBN) is an effective chemical reagent for the asymmetric reduction of 1-deuterio aldehydes to chiral 1-deuterio primary alcohols. For example, benzaldehyde-1-d is reduced to pure (S)-(+)-benzyl-1-d alcohol. A deuterated reagent prepared from α-pinene and 9-BBN-9-d was found to reduce a variety of aromatic, aliphatic, and α,β-unsaturated aldehydes to the corresponding chiral primary 1-deuterio alcohols. In each case a large excess of the R enantiomer is formed. Steric factors seem to have little effect on the extent of asymmetric induction, but electron-donating para substituents on benzaldehyde slightly decrease the enantioselectivity of the reduction. A number of other chiral-9-BBN derivatives were investigated. A model is proposed to account for the high asymmetric inductions.

Original languageEnglish (US)
Pages (from-to)2352-2355
Number of pages4
JournalJournal of the American Chemical Society
Volume101
Issue number9
StatePublished - 1979

ASJC Scopus subject areas

  • Chemistry(all)

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