Double aza-Morita-Baylis-Hillman Domino Reaction to Access Amino Derived 1,6-Dienes

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.

The aza-Morita-Baylis-Hillman reaction of electronically and sterically deactivated substrates.

The aza-Morita-Baylis-Hillman (azaMBH) reaction has been studied for electronically and sterically deactivated Michael acceptors. It is found that electronically deactivated systems can be converted with electron-rich phosphanes and pyridines as catalysts equally well. For sterically deactivated systems clearly better catalytic turnover can be achieved with pyridine catalysts. This is in accord...

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

The Morita-Baylis-Hillman reaction of acrylamide, as an activated alkene, has seen little development due to its low reactivity. We have developed the reaction using isatin derivatives with acrylamide, DABCO as a promoter and phenol as an additive in acetonitrile. The corresponding aza version with acrylate and acrylonitrile has also been developed resulting in high product yields.