Aaron M. Hartel, Ph.D.
College of Arts and Sciences
Chemistry, Physics and Geology
The aldol addition is one of the most important and most utilized carbon-carbon bond forming reactions in chemical synthesis. This reaction, between an aldehyde or ketone and a second, enolized aldehyde or ketone, results in the formation of a -hydroxycarbonyl (often referred to as an “aldol product” or “aldol”). Modern variations of the aldol reaction have allowed for enantio- and diastereoselectivity in the reaction; however, many of these methods have undesirable drawbacks such as the use of expensive chiral auxiliaries. The chiral auxiliaries require additional synthesis steps for their introduction and removal and cannot be completely recovered after the reaction is complete. Methods for the preparation of aldol products that do not involve enolate chemistry have also been developed. Here we propose the reaction of O-silylated cyanohydrin anions with epoxides as an alternative to the aldol addition for the preparation of β-hydroxycarbonyls. By taking advantage of excellent, established asymmetric epoxidations, this method allows for high degrees of enantio- and diastereoselectivity in a highly atom economical way. We report here the optimization of the reaction conditions and the initial scope and limitations of the epoxide electrophiles.
Melendez, Diamond Rose and Hartel, Aaron
"The reaction of O-silylated cyanohydrin anions with epoxides as an alternative for the enantio- and diastereoselective preparation of aldols,"
The Winthrop McNair Research Bulletin: Vol. 1
, Article 10.
Available at: http://digitalcommons.winthrop.edu/wmrb/vol1/iss1/10