Pyrrolidinyl–camphor derivatives have been proven to be efficient organocatalysts for enantioselective conjugate addition of ketones to alkylidene malonates, affording high chemical yields (up to 95 %) of the corresponding products with high to excellent levels of diastereoselectivity (up to >99:1 dr) and enantioselectivity (up to 96 % ee) under solvent‐free reaction conditions at ambient temperature.
Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7 a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical alpha,alpha-disubstituted aldehydes to beta-nitroalkenes. When this asymmetric transformation was catalyzed by organocatalyst 7 f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diastereomeric ratio (d.r.) and 99 % enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.
A series of pyrrolidine-camphor-derived organocatalysts (1-4) were designed and synthesised. These organocatalysts were used for direct α-amination of aldehydes with dialkyl azodicarboxylates to give the desired α-aminated products in high chemical yields (up to 92 %) and with high to excellent levels of stereoselectivity (up to Ͼ99 % ee). The reactions proceeded rapidly (within 5 min) with low catalyst loading (5 mol-%) at ambient temperature. Enantioselective aminations of asymmetric α,α-disubstituted aldehydes in the cata-
Tetrasubstituted PyrrolesOn the inside cover, N-protected, fully substituted pyrroles are important heteroaromatic compounds in medicinal chemistry and materials science. An efficient one-pot sequential synthesis of a diverse array of N-protected pyrrole 2,4-dicarboxylic acid derivatives is described by Kwunmin Chen and co-workers in their Full Paper on page 330 ff. The synthetic protocol starts from readily available nitroallylic acetates, amines, and a b-keto ester. The reaction is mediated by ceric ammonium nitrate and proceeds smoothly by an interesting S N 2' process and subsequent aromatization.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.