Titanium(IV) Alkoxide Ligand Exchange with α-Hydroxy Acids: The Enantioselective Aldol Addition
- 5 November 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (25) , 4011-4012
- https://doi.org/10.1021/ol0002727
Abstract
Ligand exchange of titanium(IV) alkoxides with α-hydroxy acids presents an unexpected and novel approach to enantioselective aldol additions of aldehydes and ketones. The aldol products were isolated in a high degree of syn-diastereoselectivity. High enantioselectivities were observed by using simple optically pure α-hydroxy acids in this novel aldol addition.Keywords
This publication has 15 references indexed in Scilit:
- A Versatile Approach Towards Enantiopure α-Methyl β-Hydroxy Ketones. Application to the Synthesis of (4R,5S) Sitophilure and of Its StereoisomersSynthetic Communications, 1998
- Stereocontrol in Aldol Addition - Synthesis of syn and anti 3-Hydroxy AldehydesSynthesis, 1998
- Titanium-Mediated Aldol-Tishchenko Reaction: A Stereoselective Synthesis of Differentiated anti 1,3-Diol MonoestersSynthesis, 1996
- A Simple Procedure for the Catalytic Acetalization of AldehydesAdvanced Synthesis & Catalysis, 1994
- The Aldol Reaction: Acid and General Base CatalysisPublished by Elsevier ,1991
- Synthesis of α,β-Unsaturated Carbonyl Compounds by Titanium Tetraalkoxide-Induced Aldol Condensation under Neutral ConditionsSynthesis, 1990
- Diastereo- und enantioselektive Aldolreaktionen via α-Silylketone, asymmetrische Synthese des Aggregationspheromons SitophilurAngewandte Chemie, 1988
- Acid-catalyzed enolization and aldol condensation of acetaldehydeJournal of the American Chemical Society, 1985
- Stereoselective Aldol CondensationsTopics in Stereochemistry, 1982
- Ueber den Essiggeist und einige davon abgeleitete VerbindungenJournal für Praktische Chemie, 1838