Catalytic, Enantioselective [4 + 2]-Cycloadditions of Ketene Enolates and o-Quinones: Efficient Entry to Chiral, α-Oxygenated Carboxylic Acid Derivatives
- 21 January 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (6) , 1810-1811
- https://doi.org/10.1021/ja058077g
Abstract
We report catalytic, enantioselective [4 + 2]-cycloadditions of o-quinones with ketene enolates (derived from readily available acid chlorides) using cinchona alkaloid derivatives as catalysts to produce products in high enantiomeric excess (ee) and good to excellent yields. The thermodynamic driving force for these reactions is due in part to the restoration of aromaticity to the products. The resulting chiral, bicycloadducts can be synthetically manipulated in a variety of useful ways, for example to provide a flexible synthesis of α-oxygenated carboxylic acid derivatives.Keywords
This publication has 1 reference indexed in Scilit:
- Asymmetric synthesis of (S)- and (R)-malic acid from ketene and chloralJournal of the American Chemical Society, 1982