Chiral thiourea derivatives as organocatalyts in the enantioselective Morita-Baylis-Hillman reactions

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 multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides

We have developed a multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with maleimides, which can efficiently construct functionalized cyclopentenes bearing three contiguous stereocenters in moderate to excellent yields and excellent diastereo- and enantioselectivities. A plausible mechanism has been also proposed on the basis of...

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...

Multifunctional chiral phosphines-catalyzed highly diastereoselective and enantioselective substitution of Morita-Baylis-Hillman adducts with oxazolones.

Multifunctional chiral phosphine (phosphine-thiourea type) L2-catalyzed allylic substitutions of MBH adducts 1 with oxazolones 2 produce the corresponding optically active adducts 3 in good to excellent yields and ee's as well as moderate to good de's under mild conditions. The synergistic interaction between hydrogen bond donor site and nucleophilic site has been discussed, indicating that fin...