Diethoxytriphenylphosphorane: a mild, regioselective cyclodehydrating reagent for conversion of diols to cyclic ethers: stereochemistry, synthetic utility, and scope

PL Robinson, CN Barry, JW Kelly…

Index: Robinson, Philip L.; Barry, Carey N.; Kelly, Jeffery W.; Evans, Slayton A. Journal of the American Chemical Society, 1985 , vol. 107, # 18 p. 5210 - 5219

Full Text: HTML

Citation Number: 57

Abstract

Abstract: Diethoxytriphenylphosphorane, Ph, P (OEt),, prepared by reaction of triphenylphosphine and diethyl peroxide, is a “hydrolytically active” dioxyphosphorane which promotes mild cyclodehydration (40-1 10 “C) of diols to cyclic ethers in neutral media. The regioselectivity in the closure of (S)-(+)-propane-1, 2-diol and@)-(-)-pentane-1, 4-diol with Ph, P (OEt), is high (8 1-82%) while the cyclodehydration of (S)-(+)-phenylethane-1, 2 ...

Related Articles:

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen) CoIII complexes. Practical synthesis of enantioenriched terminal epoxides …

[Schaus, Scott E.; Brandes, Bridget D.; Larrow, Jay F.; Tokunaga, Makoto; Hansen, Karl B.; Gould, Alexandra E.; Furrow, Michael E.; Jacobsen, Eric N. Journal of the American Chemical Society, 2002 , vol. 124, # 7 p. 1307 - 1315]

Synthesis, biodistribution, and primate imaging of fluorine-18 labeled 2β-carbo-1'-fluoro-2-propoxy-3β-(4-chlorophenyl) tropanes. Ligands for the imaging of dopamine …

[Xing, Dongxia; Chen, Ping; Keil, Robert; Kilts, Clinton D.; Shi, Bing; Camp, Vernon M.; Malveaux, Gene; Ely, Timothy; Owens, Michael J.; Votaw, John; Davis, Margaret; Hoffman, John M.; BaKay, Roy A. E.; Subramanian, Thygarajan; Watts, Ray L.; Goodman, Mark M. Journal of Medicinal Chemistry, 2000 , vol. 43, # 4 p. 639 - 648]

Mono-etherification of racemic propane-1, 2-diol by a tin (II) bromide catalyzed reaction with diazofluorene and a study of the Pseudomonas cepacia lipase catalyzed …

[Petursson, Sigthor; Jonsdottir, Sigridur Tetrahedron Asymmetry, 2012 , vol. 23, # 2 p. 157 - 163]

Studies on the biodegradation of fosfomycin: growth of Rhizobium huakuii PMY1 on possible intermediates synthesised chemically

[McGrath, John W.; Hammerschmidt, Friedrich; Preusser, Werner; Quinn, John P.; Schweifer, Anna Organic and Biomolecular Chemistry, 2009 , vol. 7, # 9 p. 1944 - 1953]

Chiral ruthenabicyclic complexes: Precatalysts for rapid, enantioselective, and wide-scope hydrogenation of ketones

[Matsumura, Kazuhiko; Arai, Noriyoshi; Hori, Kiyoto; Saito, Takao; Sayo, Noboru; Ohkuma, Takeshi Journal of the American Chemical Society, 2011 , vol. 133, # 28 p. 10696 - 10699]

More Articles...