[Development of acid-base organocatalysts for enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reactions via dual activation mechanism].

Enantioselective, organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman reactions: stereochemical issues.

Conscious of the importance that stereochemical issues may have on the design of efficient organocatalyts for both Morita-Baylis-Hillman and aza-Morita-Baylis-Hillman reaction we have analyzed them in this minireview. The so-called standard reactions involve "naked" enolates which therefore should lead to the syn adducts as the major products, irrespective of the E, Z stereochemistry of the eno...

Enantioselective aza-Morita-Baylis-Hillman reactions of acrylonitrile catalyzed by palladium(II) pincer complexes having C2-symmetric chiral bis(imidazoline) ligands.

Significance: This paper describes the palladiumcatalyzed enantioselective aza-Morita–Baylis–Hillman reaction of acrylonitriles with imines. The bulky pincer ligand enabled the synthesis of enantioenriched α-methylene-β-aminonitriles in high yield. Comment: The palladium–pincer complex preferably activates acrylonitrile, even in the presence of ethyl acrylate. The palladium ketenimide is a key ...

Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita− Baylis−Hillman Adducts and Sequential Organo-FLP Catalysis

Herein we report the metal-free diastereoselective frustrated Lewis pair (FLP)-catalyzed hydrogenation of azaMorita−Baylis−Hillman (aza-MBH) adducts, accessing a diverse range of stereodefined β-amino acid derivatives in excellent isolated yields (28 examples, 89% average yield, up to 90:10 d.r.). Furthermore, sequential organo-FLP catalysis has been developed. An initial organocatalyzed aza-MB...

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita-Baylis-Hillman (MBH) reactions with maleimides using a bifunctional tertiary amine, β-isocupreidine (β-ICD), as the catalyst. This route allows a convenient approa...

Recent advances in organocatalytic asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reactions.