Gnanadesikan, Vijay, et al. "Direct Catalytic Asymmetric aldol-Tishchenko Reaction." Journal of the American Chemical Society, vol. 126, no. 25, 2004, pp. 7782-3.
Gnanadesikan V, Horiuchi Y, Ohshima T, et al. Direct catalytic asymmetric aldol-Tishchenko reaction. J Am Chem Soc. 2004;126(25):7782-3.
Gnanadesikan, V., Horiuchi, Y., Ohshima, T., & Shibasaki, M. (2004). Direct catalytic asymmetric aldol-Tishchenko reaction. Journal of the American Chemical Society, 126(25), 7782-3.
Gnanadesikan V, et al. Direct Catalytic Asymmetric aldol-Tishchenko Reaction. J Am Chem Soc. 2004 Jun 30;126(25):7782-3. PubMed PMID: 15212518.
TY - JOUR
T1 - Direct catalytic asymmetric aldol-Tishchenko reaction.
AU - Gnanadesikan,Vijay,
AU - Horiuchi,Yoshihiro,
AU - Ohshima,Takashi,
AU - Shibasaki,Masakatsu,
PY - 2004/6/24/pubmed
PY - 2004/6/24/medline
PY - 2004/6/24/entrez
SP - 7782
EP - 3
JF - Journal of the American Chemical Society
JO - J Am Chem Soc
VL - 126
IS - 25
N2 - 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 using 10 mol % of the asymmetric catalyst. A variety of ketones and aldehydes, including propyl and butyl ketones, were coupled efficiently, yielding the corresponding aldol-Tishchenko products in up to 96% yield and 95% ee. Diastereoselectivity was generally below the detection limit of 1H NMR (>98:2). Preliminary studies performed to clarify the mechanism revealed that the aldol products were racemic with no diastereoselectivity. On the other hand, the Tishchenko products were obtained in a highly enantiocontrolled manner.
SN - 0002-7863
UR - https://www.unboundmedicine.com/medline/citation/15212518/Direct_catalytic_asymmetric_aldol_Tishchenko_reaction_
DB - PRIME
DP - Unbound Medicine