Synfacts 2009(4): 0441-0441  
DOI: 10.1055/s-0028-1088098
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

α-Alkylation of Aldehydes by SN1-Type Reaction of Alcohols

Contributor(s): Benjamin List, Ilija Čorić
P. G. Cozzi*, F. Benfatti, L. Zoli
Università di Bologna, Italy
Further Information

Publication History

Publication Date:
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.