1421968-82-2Relevant academic research and scientific papers
Pd(0)-Catalyzed Chemo-, Diastereo-, and Enantioselective α-Quaternary Alkylation of Branched Aldehydes
Schultz, Johnathan E.,Trost, Barry M.,Wang, Youliang,Zuo, Zhijun
, p. 9496 - 9503 (2020)
Quaternary carbon stereocenters are ubiquitous in a wide variety of organic compounds and drug molecules. Highly enantioselective construction of such quaternary carbon centers poses a singular challenge due to the steric repulsion between the four different carbon substituents. Herein, we report a novel strategy to control the enantioselective construction of chiral α-quaternary aldehydes from racemic α-branched aldehydes. Distinct from the established chiral α-quaternary aldehyde synthesis, this project employed a chiral π-allyl-Pd complex neighboring the enolate to determine both the enantio- and diastereoselectivity. The synthetic utility of the products has been highlighted by a series of derivatizations, and the potential of this method has been extended to the synthesis of chiral α-quaternary ketones. Furthermore, this reaction exemplifies the themes of step and atom economy, in addition to the principles of diversity-oriented synthesis.
Regio-and enantioselective synthesis of pyrrolidines bearing a quaternary center by palladium-catalyzed asymmetric [3 + 2] cycloaddition of trimethylenemethanes
Trost, Barry M.,Lam, Tom M.,Herbage, Melissa A.
supporting information, p. 2459 - 2461 (2013/03/29)
Herein we describe the first use of disubstituted donors in the palladium-catalyzed trimethylenemethane (TMM) cycloaddition resulting in an enantioselective synthesis of highly substituted pyrrolidines. These cyanoalkyl donors 1 form all-carbon quaternary centers in a catalytic, asymmetric, and intermolecular manner uniquely using diamidophosphite ligands L2 and L3, generating synthetically important chiral building blocks in good yields and selectivities.
