STEREOCHEMISTRY OF THE ADDITION OF α-METALLATED N,N-DIALKYLSULFONAMIDES TO ALDEHYDES

Abstract

The stereochemistry of aldol reactions of R¹CH(M)SO₂N(R)₂ and aldehydes (R²CHO) is studied under a wide variety of reaction conditions. Effects of temperature, solvent, counterion and the effect of nature and effective volume of substituents R¹ and R² are investigated. These factors do not influence markedly the stereoselectivity of the reaction, which ranges from zero to moderate. A plausible transition state structure for the formation of β-hydroxysulfonamides is discussed.

Key Words:

• N,N-dialkylamides of 1-alkyl(aryl)-2-alkyl(aryl)-2-hydroxyethanesulfonic acid
• α-metallated N,N-dialkylsulfonamides;
• aldol reaction
• stereochemistry
• configuration
• transition state.