Claisen rearrangements of equilibrating allylic azides.

作者: Donald Craig , John W. Harvey , Alexander G. O'Brien , Andrew J. P. White

DOI: 10.1039/C1OB05972F

关键词: Allyl compoundMoleculeChemistryDecarboxylationStereoisomerismAllylic rearrangementOrganic chemistry

摘要: Equilibrating mixtures of allylic azide-containing alcohols or 2-tolylsulfonylacetic esters undergo Johnson-Claisen Ireland-Claisen rearrangement reactions to give unsaturated γ-azidoesters and -acids, respectively. Decarboxylation the acids under basic conditions gives azidosulfones, with moderate high diastereoselectivity.

参考文章(50)
Scott E. Schaus, Bridget D. Brandes, Jay F. Larrow, Makoto Tokunaga, Karl B. Hansen, Alexandra E. Gould, Michael E. Furrow, Eric N. Jacobsen, Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)CoIII Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols Journal of the American Chemical Society. ,vol. 124, pp. 1307- 1315 ,(2002) , 10.1021/JA016737L
Cory C. Bausch, Jeffrey S. Johnson, Conjugate Addition/Ireland−Claisen Rearrangements of Allyl Fumarates: Simple Access to Terminally Differentiated Succinates Journal of Organic Chemistry. ,vol. 73, pp. 1575- 1577 ,(2008) , 10.1021/JO701778K
Jin K. Cha, S.C. Lewis, Diastereoselective Ireland-Claisen rearrangement of allylic alcohols Tetrahedron Letters. ,vol. 25, pp. 5263- 5266 ,(1984) , 10.1016/S0040-4039(01)81579-3
Hamed Ben Ammar, Jérôme Le Nôtre, Mansour Salem, Mohamed T. Kaddachi, Loïc Toupet, Jean-Luc Renaud, Christian Bruneau, Pierre H. Dixneuf, New [Ru3(CO)12]‐Based Catalysts with Imidazolinium Salt, Diimine, or Bis(oxazoline) Ligands and Ruthenium Bis(oxazoline) Complex for Tandem Isomerisation/Claisen Rearrangement of Dienyl Ethers − X‐ray Structure of [RuCl{(R,R)‐bis(isopropyloxazoline)}(p‐cymene)]BF4 European Journal of Inorganic Chemistry. ,vol. 2003, pp. 4055- 4064 ,(2003) , 10.1002/EJIC.200300322
Toshio Suzuki, Etsuko Sato, Shinko Kamada, Hitoshi Tada, Katsuo Unno, Tetsuii Kametani, General method for the preparation of α-methylene-γ-butyrolactones from (R)- and (S)-1,2-isopropylideneglyceraldehydes Journal of The Chemical Society-perkin Transactions 1. ,vol. 17, pp. 387- 391 ,(1986) , 10.1039/P19860000387
David Askin, Christof Angst, Samuel Danishefsky, A total synthesis of N-acetylactinobolamine Journal of Organic Chemistry. ,vol. 50, pp. 5005- 5007 ,(1985) , 10.1021/JO00224A082
Susumi Hatakeyama, Keiichi Saijo, Seiichi Takano, Enantioselective synthesis of (−)-elenolic acid and (−)-ajmalicine Tetrahedron Letters. ,vol. 26, pp. 865- 868 ,(1985) , 10.1016/S0040-4039(00)61950-0