137151-62-3Relevant academic research and scientific papers
Highly regioselective [3,3] rearrangement of aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin complex, Cr(TPP)Cl
Takanami, Toshikatsu,Hayashi, Mikiko,Iso, Kazuhiro,Nakamoto, Hirose,Suda, Kohji
, p. 9467 - 9474 (2007/10/03)
The Claisen rearrangement of simple aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin, Cr(TPP)Cl, is described. The porphyrin-based Lewis acid catalyst can effectively accelerate the rearrangement via a concerted [3,3] pathway with a minimal degree of bond ionization of the substrates, providing the corresponding Claisen products in moderate to high yields and almost perfect regioselectivity at low catalyst loading.
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.
