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

Maleimide as an efficient nucleophilic partner in the aza-Morita-Baylis-Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles.

A highly enantioselective Morita-Baylis-Hillman reaction of maleimides with isatin derived ketimines has been developed to obtain enantiomerically enriched 3-substituted-3-aminooxindoles using β-isocupreidine as an organocatalyst. Maleimide acting as a nucleophile provides products with up to 99% ee.

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...