69248-37-9Relevant academic research and scientific papers
Chiral Supramolecular U-Shaped Catalysts Induce the Multiselective Diels-Alder Reaction of Propargyl Aldehyde
Hatano, Manabu,Sakamoto, Tatsuhiro,Mizuno, Tomokazu,Goto, Yuta,Ishihara, Kazuaki
supporting information, p. 16253 - 16263 (2018/11/27)
The Diels-Alder reaction, which is a traditional [4 + 2] cycloaddition with two carbon-carbon bond formations, is one of the most powerful tools to synthesize versatile and unique six-membered rings. We show that chiral supramolecular U-shaped boron Lewis acid catalysts promote the unprecedented multiselective Diels-Alder reaction of propargyl aldehyde with cyclic dienes. Independent from the substrate control, enantio-, endo/exo-, π-facial-, regio-, site-, and substrate-selectivities could be controlled by the present U-shaped catalysts. The obtained reaction products could access the concise synthesis of chiral diene ligands and a key intermediate of (+)-sarkomycin. The results presented here might partially contribute to the development of artificial enzyme-like supramolecular catalysts for multiselective reactions, which will be able to target organic compounds that have thus far eluded synthesis.
Formation and synthetic utility of benzyl- and phenyl-cyclopentadienylthallium
Singh, Poonam,Rausch, Marvin D.,Bitterwolf, Thomas E.
, p. 273 - 282 (2007/10/02)
Benzyl- and phenyl-cyclopentadiene have been shown to react with thallium ethoxide in ethanol to give the corresponding benzyl- and phenyl-cyclopentadienylthallium compounds in excellent yield.These reagents are air stable for brief periods, have extended shelf-lives, and have been shown to be superior starting materials for the synthesis of a variety of cyclopentadienylmetal complexes.
