203449-13-2Relevant academic research and scientific papers
SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction
Diagne, Abdallah B.,Li, Shuheng,Perkowski, Gregory A.,Mrksich, Milan,Thomson, Regan J.
supporting information, p. 658 - 662 (2015/11/17)
Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.
Application of in situ-generated Rh-bound trimethylenemethane variants to the synthesis of 3,4-fused pyrroles
Schultz, Erica E.,Sarpong, Richmond
, p. 4696 - 4699 (2013/05/09)
Rh-bound trimethylenemethane variants generated from the interaction of a Rh-carbenoid with an allene have been applied to the synthesis of substituted 3,4-fused pyrroles. The pyrrole products are useful starting points for the syntheses of various dipyrromethene ligands. Furthermore, the methodology has been applied to a synthesis of the natural product cycloprodigiosin, which demonstrates antitumor and immunosuppressor activity.
An Intramolecular Allenic [2 + 2 + 1] Cycloaddition
Brummond, Kay M.,Wan, Honghe,Kent, Joseph L.
, p. 6535 - 6545 (2007/10/03)
A new stereo- and regioselective method for the preparation of α-methylene and 4-alkylidene cyclopentenones is described. These substructures were achieved by an intramolecular [2 + 2 + 1] cycloaddition of an allene, alkyne, and carbon monoxide moieties to afford the target compounds stereoselectively and in good yields. In some cases, the target compounds were obtained as mixtures, but it is demonstrated that the formation of either the α-methylene or 4-alkylidene cyclopentenone can be controlled by the allene structure or reaction conditions. Monosubstituted allenes afford α-methylene cyclopentenones as the only cycloadduct. Disubstitution on the allene alters the course of the allenic [2 + 2 + 1] reaction. 3,3-Disubstituted allenes undergo cycloaddition with the least substituted π-bond of the allene. This affords the bicyclo[4.3.0]nonane ring system. Cycloaddition of 1,3-disubstituted allenes afford mixtures of several possible cycloadducts. However, it has been shown that good control over the product ratio can be obtained by altering the cycloaddition conditions and that the regiochemistry can be directed depending upon the metal used.
