Asymmetric reduction of prochiral aromatic ketones by Borane–Amine complexes in the presence of a chiral amine–BF3catalyst
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 17,p. 1145-1147
- https://doi.org/10.1039/c39900001145
Abstract
The (–)-N-α-Methylbenzyl-3,5-dihydrodinaphthazepine–BH3 complex reduces aromatic ketones to alcohols with 11–57% enantiomeric excess (e.e.) in the presence of BF3·OEt2, the (–)-N-α-methylbenzyl-3,5 dihydrodinaphthazepine–BF3 complex catalyses asymmetric reduction of acetophenone by N,N′-diethylaniline–BH3 to give α-phenylethyl alcohol in 51% e.e.Keywords
This publication has 6 references indexed in Scilit:
- C2 symmetry and asymmetric inductionChemical Reviews, 1989
- Hydroboration of prochiral olefins with chiral Lewis base–borane complexes: relationship to the mechanism of hydroborationJournal of the Chemical Society, Chemical Communications, 1987
- Enantioselective carboxylation of a prochiral enolate in the presence of a chiral lithium amideTetrahedron Letters, 1986
- Selective reductions. 29. A simple technique to achieve an enhanced rate of reduction of representative organic compounds by borane-dimethyl sulfideThe Journal of Organic Chemistry, 1982
- Asymmetric induction. Part 3. Asymmetric reduction of ketones with amine-boranes in the presence of acidsJournal of the Chemical Society, Perkin Transactions 1, 1981
- CVII.—Investigations on the dependence of rotatory power on chemical constitution. Part VI. The optical rotatory power of methyl-tert.-butyl-, methylbenzyl-, methylphenylethyl- and methyl-α-naphthyl-carbinolsJournal of the Chemical Society, Transactions, 1914