Chiral catalyst controlled addition of dialkylzincs to chiral α-siloxyaldehydes; asymmetric synthesis of either diastereoisomer of mono-protected vicinal diols
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 5,p. 567-568
- https://doi.org/10.1039/c39940000567
Abstract
The extent of the asymmetric addition of dialkylzincs to chiral α-siloxyaldehydes is determined by the configuration of the chiral catalyst and not by the chirality of α-siloxyaldehydes, providing either diastereoisomer of mono-protected vicinal diols in high diastereoisomeric excess.Keywords
This publication has 15 references indexed in Scilit:
- Enantioselective addition of organozinc reagents to aldehydesChemical Reviews, 1992
- Stereoselective synthesis of optically active syn- and anti-1,3-diols by the catalytic alkylation of a β-alkoxy aldehydeJournal of the Chemical Society, Chemical Communications, 1992
- Enantioselective conjugate addition of diethylzinc to enones using chiral β-aminoalcohol as chiral catalyst or ligandTetrahedron Letters, 1991
- Enantioselective epoxidation of unfunctionalized simple olefins by non-racemic molybdenum(VI)(oxo-diperoxo) complexesJournal of Organometallic Chemistry, 1989
- Asymmetric synthesis of optically active β-substituted ketones by highly enantioselective catalytic conjugate addition of dialkylzinc reagents to enones using a catalyst system of nickel(II)-chiral ligand–achiral ligand in acetonitrile/tolueneJournal of the Chemical Society, Chemical Communications, 1989
- A new chiral catalyst for the highly enantioselective addition of dialkylzinc reagents to aliphatic aldehydesJournal of the Chemical Society, Chemical Communications, 1987
- Non-chelation-controlled nucleophilic addition to chiral α-siloxyketonesJournal of the Chemical Society, Chemical Communications, 1986
- Chelation or Non‐Chelation Control in Addition Reactions of Chiral α‐ and β‐ Alkoxy Carbonyl Compounds [New Synthetic Methods (44)]Angewandte Chemie International Edition in English, 1984
- Chelation or Non‐Chelation Control in Stereoselective Reactions of Titanium Reagents with Chiral Alkoxycarbonyl CompoundsAngewandte Chemie International Edition in English, 1983
- Biomimetic polyene cyclizations. Asymmetric induction in the cyclization of a dienic acetalJournal of the American Chemical Society, 1976