Bifunctional Organocatalysts for Enantioselective aza-Morita-Baylis-Hillman (aza-MBH) Reactions

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

This review describes our recent efforts in the development of acid-base organocatalysts, (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl) BINOL (6a) and (S)-3-[2-(diphenylphosphino)phenyl] BINOL (13a), with dual activation mechanism for the aza-Morita-Baylis-Hillman (aza-MBH) reaction. In these catalysts, chiral Brønsted acid units are connected with a Lewis base unit via a spacer. The acid-base m...

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...

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

Chiral phosphine Lewis bases in catalytic, asymmetric aza-Morita–Baylis–Hillman reaction*

In the aza-Morita–Baylis–Hillman reaction of N-sulfonated imines with methyl vinyl ketone (MVK) promoted by chiral phosphine Lewis base: (R)-2'-diphenylphosphanyl[1,1']binaphthalenyl-2-ol (LB1) (10 mol %), the aza-Morita–Baylis–Hillman adducts were obtained in good yields with high ee (70–94 % ee) at –30 °C in THF. The scope and limitations of this reaction have been disclosed.

A way to highly enantiomerically enriched aza-Morita-Baylis-Hillman-type products.