63974-05-0Relevant articles and documents
A chiral bidentate sp2-N ligand, naph-diPIM: Application to CpRu-catalyzed asymmetric dehydrative C-, N-, and O-allylation
Miyata, Kengo,Kutsuna, Hironori,Kawakami, Sho,Kitamura, Masato
supporting information; scheme or table, p. 4649 - 4653 (2011/06/27)
A handy new ligand: The CpRu complex (Cp=cyclopentadienyl) of a new type of chiral bisamidine ligand with a naphtho[1,2-b:7,8-b]dipyrroloimidazole (Naph-diPIM) skeleton with a Bronsted acid efficiently catalyzes dehydrative intermolecular C-allylation with high enantio- and regioselectivity. The catalytic system also gives nearly enantiomerically pure cycloalkanes and N- and O-heterocycles with a substrate/catalyst ratios of up to 10 000.
Cyclopropenium-activated cyclodehydration of diols
Kelly, Brendan D.,Lambert, Tristan H.
, p. 740 - 743 (2011/05/04)
The dehydrative cyclization of diols to cyclic ethers via cyclopropenium activation is described. Using 2,3-diphenylcyclopropene and methanesulfonic anhydride, a series of 1,4-and 1,5-diols are rapidly cyclized to furnish tetrahydrofurans and tetrahydropyrans in high yield. Eleven total substrates are shown, including a gram scale cyclization of a diterpene derivative.
Asymmetrie dehydrative cyclization of ω-hydroxy allyl alcohols catalyzed by ruthenium complexes
Tanaka, Shinji,Seki, Tomoaki,Kitamura, Masato
supporting information; experimental part, p. 8948 - 8951 (2010/02/27)
New axially chiral ligands and their allyl esters have been designed and synthesized. The combination of these ligands with [CpRu(CH3CN)3]PF6 has realized highly efficient intramolecular dehydrative cylization of w-hydroxy allyl alcohols, to give a-alkeny
Reactions of 6,8-Dioxabicyclo(3.2.1)oct-3-ene and 6,8-Dioxabicyclo(3.2.1)oct-2-ene with Lithium Aluminium Hydride
Majumdar, K. C.,Ranganayakulu, K.,Brown, R. K.
, p. 303 - 306 (2007/10/02)
Reduction of 6,8-dioxabicyclo(3.2.1)oct-3-ene (6) with lithium aluminium hydride in refluxing 1,2-dimethoxyethane gives 2-hydroxymethyl-3,4-dihydro-2H-pyran (7) in an excellent yield.However, under identical conditions 6,8-dioxabicyclo(3.2.1)oct-2-ene (8) gives a mixture of 4-hexen-1-ol (9), 5-hexen-1-ol (10) and 2-hexene-1,6-diol (11).When 6 is refluxed with LAH in di-n-propyl ether, 7 is obtained in addition to 2-hydroxymethyl-2,3-dihydro-6H-pyran (33).However, compound 8 remains unaffected by LAH under similar conditions.