116183-29-0Relevant academic research and scientific papers
Reductive aldol-type reaction of α,β-unsaturated esters with aldehydes or ketones in the presence of Rh catalyst and Et2Zn
Sato, Kazuyuki,Isoda, Motoyuki,Tokura, Yoriko,Omura, Keiko,Tarui, Atsushi,Omote, Masaaki,Kumadaki, Itsumaro,Ando, Akira
, p. 5913 - 5915 (2013/10/21)
The reaction of RhCl(PPh3)3 with Et2Zn easily generated a rhodium-hydride complex (Rh-H) that added to α,β-unsaturated esters to form rhodium enolate complexes by formal 1,4-reduction. These rhodium enolates gave the corre
Catalytic generation of activated carboxylates: Direct, stereoselective synthesis β-hydroxyesters from epoxyaldehydes
Chow, Kenneth Yu-Kin,Bode, Jeffrey W.
, p. 8126 - 8127 (2007/10/03)
The catalytic generation of activated carboxylates from epoxyaldehydes enables the direct, stereoselective synthesis of β-hydroxyesters under mild, convenient reaction conditions. In addition to providing a new method for the synthesis of anti-aldol adducts, this chemistry unveils a mechanistically viable solution to the catalytic, waste-free synthesis of esters. Copyright
Chemistry of enoxysilacyclobutanes: Highly selective uncatalyzed aldol additions
Denmark, Scott E.,Griedel, Brian D.,Coe, Diane M.,Schnute, Mark E.
, p. 7026 - 7043 (2007/10/02)
O-(Silacyclobutyl) ketene acetals derived from esters, thiol esters, and amides underwent facile aldol addition with a variety of aldehydes at room temperature without the need for catalysts. The uncatalyzed aldol addition reaction of O-(silacyclobutyl) ketene acetals displayed the following characteristics: (1) the rate of reaction was highly dependent on the spectator substituent on silicon and the geometry of the ketene acetal, (2) the O,O-ketene acetal of E configuration afforded the syn aldol products with high diastereoselectivity (93/7 to 99/1), (3) conjugated aldehydes reacted more rapidly than aliphatic aldehydes, and (4) the reaction was mildly sensitive to solvent. In addition, the aldol reaction was found to be efficiently catalyzed by metal alkoxides. Labeling experiments revealed that the thermal aldol reaction proceeds by direct intramolecular silicon group transfer, while the alkoxide-catalyzed version probably proceeds via in situ generated metal enolates. Computational modeling of the transition states suggests that the boat transition structures are preferred, supporting the observed syn selectivity of the thermal aldol reaction. Both thermal and alkoxide-catalyzed Michael additions were investigated, revealing a competition between 1,2- and 1,4-addition favoring the former.
Chemistry of Ketene Acetals. Part 8. Stereochemistry of the Reaction of 1,1-Dimethoxypropene with Aldehydes
Hofstraat, Rob G.,Scheeren, Hans W.,Nivard, Rutger J. F.
, p. 561 - 564 (2007/10/02)
The Lewis acid-catalysed (2+2)cycloadditions of 1,1-dimethoxypropene with various aldehydes RCHO have been studied.These reactions, which are supposed to proceed via dipolar intermediates, yield 2,2-dimethoxyoxetanes, the formation of which is reversible
