Enantioselective Borane Reduction of Ketones Catalyzed by a Chiral Oxazaphospholidine Borane Complex
- 1 February 1993
- journal article
- research article
- Published by Taylor & Francis in Phosphorus, Sulfur, and Silicon and the Related Elements
- Vol. 75 (1-4) , 43-46
- https://doi.org/10.1080/10426509308037360
Abstract
The borane complex of (2R,4S)-2-phenyl-1,3,2- oxazaphospholidine 2 was readily synthetized. This complex can be used as catalyst in enantioselective reduction of ketones in toluene, with BH3:THF (or BH3:SMe2) as reducing agent. The catalytic reduction of iso-propyl methyl ketone yields (R)-3-methyl-2-butanol in 92% e.e. and 100% conversion. Reduction of different ketones under stoichiometric conditions gives the corresponding alcohols in e.e. = 99%.Keywords
This publication has 6 references indexed in Scilit:
- Enantioselective borane reduction of ketones catalysed by a chiral oxazaphospholidine–borane complexJournal of the Chemical Society, Chemical Communications, 1992
- A new chiral ligand for the asymmetric conjugate addition of organocopper reagents to enonesJournal of the American Chemical Society, 1991
- Efficient asymmetric synthesis of optically pure tertiary mono and diphosphine ligandsTetrahedron Letters, 1990
- Stereoselective synthesis of (Rp)-benzylphenyl-[2-(S)-bromomethylpyrrolidine-1-yl]phosphine oxide from (S)-(+)-prolinol by the Michaelis–Arbuzov reaction: application in the synthesis of a chiral hybrid phosphine–phosphine oxide ligandJournal of the Chemical Society, Chemical Communications, 1989
- Asymmetric carbonylation of .alpha.-methylbenzyl bromide catalyzed by oxazaphospholane-palladium complexes under phase-transfer conditionsOrganometallics, 1988
- Asymmetrische Synthese von 2‐Organo‐1,3,2‐oxazaphospholidinenEuropean Journal of Inorganic Chemistry, 1984