The phosphonate-phosphate and phosphate-phosphonate rearrangement and their applications V. On the reaction ofs-butyllithium/TMEDA with symmetrical trialkyl phosphates

作者: F. Hammerschmidt , S. Schmidt

DOI: 10.1007/BF00807567

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摘要: 1-(Tributylstannyl)hexanol ((±)-8 is phosphorylated to give phosphate (±)-9 which then transmetallated. The organolithium intermediate (±)-10 isomerizes α-hydroxyphosphonate (±)-12. Similar intermediates are also formed upon direct deprotonation of triethyl, tri-n-propyl, and tri-n-butyl phosphate, subsequently rearrange α-hydroxyphosphonates (±)-14a–c.

参考文章(18)
D. Hoppe, H. Ahrens, W. Guarnieri, H. Helmke, S. Kolczewski, Heteroatom-directed lithiations of chiral alkyl carbamates: A powerful tool for enantioselective synthesis Pure and Applied Chemistry. ,vol. 68, pp. 613- 618 ,(1996) , 10.1351/PAC199668030613
Friedrich Hammerschmidt, Horst Völlenkle, Zur Stereochemie der Phosphat‐Phosphonat‐Umlagerung European Journal of Organic Chemistry. ,vol. 1986, pp. 2053- 2064 ,(1986) , 10.1002/JLAC.198619861202
Peter Beak, Amit Basu, Donald J. Gallagher, Yong Sun Park, S. Thayumanavan, Regioselective, Diastereoselective, and Enantioselective Lithiation−Substitution Sequences: Reaction Pathways and Synthetic Applications Accounts of Chemical Research. ,vol. 29, pp. 552- 560 ,(1996) , 10.1021/AR950142B
A. N. Pudovik, I. V. Konovalova, Addition Reactions of Esters of Phosphorus(III) Acids with Unsaturated Systems Synthesis. ,vol. 1979, pp. 81- 96 ,(1979) , 10.1055/S-1979-28566
William G. Kofron, Leona M. Baclawski, A convenient method for estimation of alkyllithium concentrations Journal of Organic Chemistry. ,vol. 41, pp. 1879- 1880 ,(1976) , 10.1021/JO00872A047