868705-46-8Relevant academic research and scientific papers
A concise synthesis of carpanone using solid-supported reagents and scavengers
Baxendale, Ian R.,Lee, Ai-Lan,Ley, Steven V.
, p. 1850 - 1857 (2002)
The synthesis of the natural product carpanone by utilization of polymer supported reagents, eliminating the need for conventional purification techniques was reported. The synthesis and crystal structure of a polymer-supported iridium catalyst for isomerization was also reported. The observations showed that isomerization of electron-rich aromatic compounds by the catalyst resulted in products with predominantly trans alkene geometry. However, the electron-poor derivatives were found to be less prone to rearrangement.
Stereoselective isomerization of unsymmetrical diallyl ethers to allyl (E)-vinyl ethers by a cationic iridium catalyst
Yamamoto, Yasunori,Fujikawa, Ryou,Miyaura, Norio
, p. 2383 - 2391 (2000)
The stereoselective isomerization of unsymmetrical diallyl ethers to allyl (E)-vinyl ethers was carried out in the presence of a cationic iridium(I) catalyst. The catalyst prepared in situ by treating [Ir(cod)(PPh2Me)2]PF6 with hydrogen was found to be an excellent catalyst to selectively isomerize the less substituted allyl group to an (E)-vinyl ether.
Transition-metal-mediated cascade reactions: The water-accelerated carboalumination-Claisen rearrangement-carbonyl addition reaction
Wipf, Peter,Waller, David L.,Reeves, Jonathan T.
, p. 8096 - 8102 (2007/10/03)
A three-step cascade reaction involving a water-accelerated catalytic carboalumination, a Claisen rearrangement, and a nucleophilic carbonyl addition converts terminal alkynes and allyl vinyl ethers into allylic alcohols containing up to three contiguous asymmetric carbon centers. Stoichiometric quantities of water as an additive increase the rate of the [3,3] sigmatropic rearrangement as well as the diastereoselectivity of the carbonyl addition process. Reaction products contain 1,6-diene functionalities that are readily cyclized to substituted cyclopentenes. An extension of this methodology to a sequence involving a [1,3] sigmatropic shift was feasible with a cyclopropylmethyl vinyl ether substrate.
