14869-02-4Relevant academic research and scientific papers
The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex
Mukherjee, Paramita,Widenhoefer, Ross A.
supporting information, p. 3437 - 3444 (2013/07/05)
A 1:1 mixture of [AuCl(IPr)] (IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidine) and AgClO4 catalyzes the intermolecular dehydrative alkoxylation of primary and secondary allylic alcohols with aliphatic primary and secondary alcohols to for
Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols
Li, Zhanjie,Parr, Brendan T.,Davies, Huw M. L.
supporting information; experimental part, p. 10942 - 10946 (2012/08/07)
The tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor rhodium carbenoids and chiral allyl alcohols is a convergent C-C bond forming process, which generates two vicinal stereogenic centers. Any of the four possible stereoisomers can be selectively synthesized by appropriate combination of the chiral catalyst Rh2(DOSP)4 and the chiral alcohol.
Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols
Harada, Susumu,Kowase, Noboru,Tabuchi, Nobuhito,Taguchi, Takeo,Dobashi, Yasuo,Dobashi, Akira,Hanzawa, Yuji
, p. 753 - 766 (2007/10/03)
Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1- butenyl)oxirane and vinyloxirane with Cp2ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp2ZrHCl.
Formation of cyclopropyl carbinols through a highly diastereoselective hydrozirconation of vinyloxirane derivatives
Harada, Susumu,Kowase, Noboru,Taguchi, Takeo,Hanzawa, Yuji
, p. 1957 - 1960 (2007/10/03)
Cyclopropyl carbinol derivatives were efficiently prepared through a highly diastereoseletive hydrozirconation of vinyloxiranes and the intramolecular attack of the generated alkylzirconocene with the inversion of the configuration at the reacting oxirane carbon.
A Simple Preparation of Five-Carbon Chiral Allylic and Homoallylic Alcohol Synthons
Takano, Seiichi,Sekiguchi, Yoshinori,Sato, Nobuaki,Ogasawara, Kunio
, p. 139 - 141 (2007/10/02)
Five-carbon homoallylic and allylic alcohols 4, 5, and 6, potentially useful building blocks for the syntheses of a wide variety of optically active compounds, are prepared from chiral (S)-O-benzylglycidol (1) via the selective formation of the terminal a
Versatile Chiral Building Blocks bearing a Secondary Methyl Group from (S)-O-benzylglycidol (Benzyloxymethyloxirane)
Takano, Seiichi,Sekiguchi, Yoshinori,Ogasawara, Kunio
, p. 555 - 557 (2007/10/02)
Versatile chiral building blocks for the construction of chiral natural products bearing a secondary methyl group have been efficiently prepared from (S)-O-benzylglycidol.
