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α-Alkylation of Aldehydes by SN1-Type Reaction of Alcohols
P. G. Cozzi*, F. Benfatti, L. Zoli
Università di Bologna, Italy
23 March 2009 (online)
Alcohols capable of forming stabilized carbocations were used as the alkylating reagents for aldehydes. A catalytic amount of secondary amine salt 1 in Et2O gave α-alkylated aldehydes 2 in moderate to good yields and good enantioselectivity with H2O being the only byproduct. In this simple procedure the ammonium salt acts as an aminocatalyst but also as an acid to generate the carbocation from the alcohol.