Asymmetric synthesis of alpha substituted benzyl alcohols via the stereoselective addition of nucleophiles to homochiral tricarbonyl(η6-o-trialkylsilylbenzaldehyde)chromium(0) complexes
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 393-407
- https://doi.org/10.1039/p19900000393
Abstract
The addition of nucleophiles to tricarbonyl(η6-o-trialkylsilylbenzaldehyde)chromium(0) complexes proceeds with complementary diastereoselectivities in the presence or absence of strong Lewis acids. The ready availability of homochiral aldehyde complexes, via classical resolution with L-valinol, permits the synthesis of alpha substituted benzyl alcohols with high enantiomeric excesses.Keywords
This publication has 20 references indexed in Scilit:
- Asymmetric synthesis of α-substituted o-methoxybenzyl alcohols via stereoselective additions to kinetically resolved o-anisaldehyde(tricarbonyl)chromiumJournal of the Chemical Society, Perkin Transactions 1, 1989
- Reaction de Reformatsky diastéréospécifique sur un aldéhyde arène chrome tricarbonyle chiralJournal of Organometallic Chemistry, 1987
- Asymmetric synthesis of ephedrine analogsJournal of Organometallic Chemistry, 1987
- Highly Diastereoselective Synthesis of Aminoalcohols of Ephedrine TypeChemistry Letters, 1987
- Stereoselective addition reaction of diethylzinc to aldehydes, catalyzed by cinchona alkaloidsThe Journal of Organic Chemistry, 1987
- Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydesJournal of the American Chemical Society, 1986
- Stereoselective synthesis of (.eta.6-arene)Cr(CO)3 complexes possessing a chiral center at the benzylic positionThe Journal of Organic Chemistry, 1986
- Tricarbonylchrom‐Komplexe von Aryltrimethylsilanen – Darstellung und ReaktionenEuropean Journal of Inorganic Chemistry, 1985
- Asymmetric addition of perfluoroalkyl groups on carbonyls with zinc and ultrasoundTetrahedron Letters, 1984
- Exemples d'induction asymétrique en série du benchrotrèneJournal of Organometallic Chemistry, 1972