Direct Catalytic Asymmetric Aldol-Tishchenko Reaction
Vijay Gnanadesikan, Yoshihiro Horiuchi, Takashi Ohshima and Masakatsu Shibasaki*
*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo
113-0033, Japan, Email: mshibasa
mol.f.u-tokyo.ac.jp
V. Gnanadesikan, Y. Horiuchi, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc., 2004, 126, 7782-7783.
DOI: 10.1021/ja047906f (free Supporting Information)
Abstract
A direct catalytic asymmetric aldol reaction of propionate equivalent was achieved via the aldol-Tishchenko reaction. Coupling an irreversible Tishchenko reaction to a reversible aldol reaction overcame the retro-aldol reaction problem and thereby afforded the products in high enantio and diastereoselectivity.
see article for more examples
proposed mechanism
Key Words
Tishchenko Reaction, 1,3-Diols
ID: J48-Y2004-1520
