Intermolecular Oxonium Ylide Mediated Synthesis of Medium-Sized Oxacycles
摘要:
Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.
SCHOBERT, RAINER, ANGEW. CHEM., 100,(1988) N, C. 869-871
作者:SCHOBERT, RAINER
DOI:——
日期:——
Prevost, Bulletin de la Societe Chimique de France, 1941, vol. <5>8, p. 96
作者:Prevost
DOI:——
日期:——
[EN] ISOMERIZATION OF ALK-2-ENYL ETHERS
申请人:GAF CHEMICALS CORPORATION
公开号:WO1991003449A1
公开(公告)日:1991-03-21
(EN) This invention is directed to a process for the isomerization of alk-2-enyl ethers to the corresponding alk-1-enyl ethers under anhydrous conditions by the use of a supported rare metal catalyst atomic number 44 or 45 which comprises contacting the allyl ether with between about 0.1 and about 20 wt. % of said supported catalyst in which the amount of rare metal with respect to support is between about 0.05 and about 10 wt. %.(FR) Cette invention concerne un procédé pour l'isomérisation d'éthers alk-2-ényle aux éthers alk-1-ényle correspondants, dans des conditions anhydres, au moyen d'un catalyseur porté par un métal rare de nombre atomique 44 ou 45 qui comprend, au contact de l'éther allyle, entre environ 0,1 et environ 20 % en poids dudit catalyseur porté, pour lequel la quantité de métal rare par rapport au support se situe entre environ 0,05 et environ 10 % en poids.
Intermolecular Oxonium Ylide Mediated Synthesis of Medium-Sized Oxacycles
作者:Daniel J. Mack、Lindsay A. Batory、Jon T. Njardarson
DOI:10.1021/ol203129d
日期:2012.1.6
Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.