An array of N-tosylated α-aminoalkylallenic esters was prepared and their cyclization under the influence of nucleophilic phosphine catalysts was explored. The α-aminoalkylallenic esters were prepared through aza-Baylis-Hillman reactions or novel DABCO-mediated decarboxylative rearrangements of allenylic carbamates. Conversion of these substrates to 3-carbethoxy-2-alkyl-3-pyrrolines was facilit...

A series of air-stable ferrocenylphosphines LB1-LB8 were designed and prepared in high yields. (R,SFc)-ferrocenylphosphine LB5 was found to efficiently promote the asymmetric [3 + 2] cycloaddition of Morita-Baylis-Hillman carbonates with maleimides to afford the corresponding bicyclic imides with 84-99% ee and 67-99% yield. Interestingly, the configuration of these products was contrary to thos...

Non-steroidal anti-inflammatory drugs play a major role in pain management. This article discusses the synthesis of thio-Pyrimidine, Benzoxazole, Benzothiazole and Triazole Analogues from Baylis-Hillman Bromides and their in-vitro testing for the activity of cyclooxygenase (COX) inhibition. The results are very encouraging and we can proceed for further investigations regarding their safety, in...

Abstract Structurally diverse fused polycyclic pyrrolo[3,2- c ]quinolinone/pyrrolizino[2,3- ]quinolinone hybrids were synthesized to get excellent yields via a tandem multi-component reaction sequence employing an environmentally benign solid state melt involving [3+2]-cycloaddition process followed by two consecutive annulation steps. Baylis–Hillman products, used as dipolarophiles, from vario...

Reactions of(4S,5R)-1-(3,4-Dimethyl-2-oxo-5-phenylimidazolidine)carbonyl-isocyanate (4) with appropriate Baylis-Hillman adducts 5 gave the corresponding acyl carbamates 6,7 as equimolar diastereomeric mixtures. These mixtures were treated with DABCO, to afford with moderate diastereoselection easily separable [2-(3",4"-dimethyl-2"-oxo-5"-phenylimidazolidine-1-carboxamido)(aryl)methyl]acrylates ...

The first asymmetric organocatalytic allylic alkylation of 1,2-dihydro-Reissert compounds and Morita-Baylis-Hillman (MBH) carbonates has been developed, which provided a novel protocol to construct enantioenriched functionalized 1,2-dihydroisoquinolines bearing vicinal quaternary and tertiary chiral centers at C-1 position (up to 94% ee, dr > 20 : 1).

An interesting new approach was developed for the synthesis of Evans' chiral auxiliaries with excellent yields. In turn, another new stereoselective and efficient strategy has also allowed for the preparation of a 2-oxazolidinone derivative in 34% overall yield from the Morita-Baylis-Hillman adduct. The antibacterial activity of this oxazolidinone was tested against Staphylococcus aureus strain...

Ein direkter C-C-Kupplungsprozess, bei dem Michael-Akzeptoren und Eschenmosersalz zusammengeführt werden, wird vorgestellt. Obwohl er an die Morita-Baylis-Hillman-Reaktion erinnert, benötigt dieser Prozess keinen Lewis-Base-Katalysator. Der zugrundeliegende Mechanismus konnte durch eine Kombination aus kinetischen Isotopenmarkierungsexperimenten computergestützten Untersuchungen aufgeklärt krit...

A Morita-Baylis-Hillman (MBH) reaction catalyzed by thiourea was monitored by ESI-MS(/MS) and key intermediates were intercepted and characterized. These intermediates suggest that thiourea acts as an organocatalyst in all steps of the MBH reaction cycle, including the rate-limiting proton-transfer step. DFT calculations, performed for a model MBH reaction between formaldehyde and acrolein with...