58547-18-5Relevant articles and documents
Improved conditions for the proline-catalyzed aldol reaction of acetone with aliphatic aldehydes
Martínez, Alberto,Zumbansen, Kristina,D?hring, Arno,Van Gemmeren, Manuel,List, Benjamin
supporting information, p. 932 - 934 (2014/05/06)
The proline-catalyzed asymmetric aldol reaction between aliphatic aldehydes and acetone has, to date, remained underdeveloped. Challenges in controlling this reaction include avoiding undesired side reactions such as aldol condensation and self-aldolization. In recent years we have developed optimized conditions, which enable high yields and good to excellent enantioselectivities, and which are presented in this communication. Georg Thieme Verlag Stuttgart New York.
Decarboxylative aldol reactions of allyl β-keto Esters via heterobimetallic catalysis
Lou, Sha,Westbrook, John A.,Schaus, Scott E.
, p. 11440 - 11441 (2007/10/03)
Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions involving allyl β-keto esters have been developed. The reaction is promoted by Pd(0)- and Yb(III)-DIOP complexes at room temperature and involves the in situ formation of a ketone enolate from allyl β-keto esters followed by addition of the enolate to aldehydes. The reaction is a new example of heterobimetallic catalysis in which the optimized reaction conditions require the addition of both metals. Copyright
Chemically reactive immunogens lead to functional convergence of the immune response
Shulman,Makarov,Ogawa,Romesberg,Keinan
, p. 10743 - 10753 (2007/10/03)
An aldolase antibody, 24H6, which was obtained from immunization with the large hapten 2, is shown to possess an active-site lysine residue with a perturbed pK(a) of 7.0. This antibody catalyzes both the aldol addition and the retrograde aldol fragmentation with a broad range of substrates that are structurally different from the hapten. This observation suggests that in reactive immunization with 1,3-diketones, the hapten structure governs the chemistry but not the overall organization of the active site. Hammett correlation studies of the 38C2- and 24H6-catalyzed aldol and retroaldol reactions revealed that although the two antibodies exhibit broad substrate specificities, they utilize slightly different mechanisms. While antibody 38C2 adopts a mechanism that is reminiscent of an acid-catalyzed aldol reaction, antibody 24H6 follows a mechanism that is similar to the base-catalyzed reaction.