Synlett, Table of Contents LETTER © Georg Thieme Verlag Stuttgart · New York Novel Synthesis of O-Allylated Oxime Ethers Based on Allylic Substitution with Oximes Hideto Miyabea, Akira Matsumuraa, Kazumasa Yoshidaa, Masashige Yamauchib, Yoshiji Takemoto*a a Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, JapanFax: +81(75)7534569; e-Mail: takemoto@pharm.kyoto-u.ac.jp; b Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-0295, Japan Recommend Article Abstract Buy Article All articles of this category Abstract The palladium or iridium-catalyzed O-allylic substitution of oximes provides a new method for direct preparation of the O-allylated oxime ethers from oximes. Key words allylic substitution - palladium - iridium - oxime - oxime ether Full Text References References For some examples of the addition of organometallic nucleophiles to the oxime ethers, see: 1a Cooper TS. Laurent P. Moody CJ. Takle AK. Org. Biomol. Chem. 2004, 2: 265 1b Moody CJ. Lightfoot AP. Gallagher PT. Synlett 1997, 659 1c Marco JA. Carda M. Murga J. González F. Falomir E. Tetrahedron Lett. 1997, 38: 1841 1d Hanessian S. Lu P.-P. Sanceau J.-Y. Chemla P. Gohda K. Fonne-Pfister R. Prade L. Cowan-Jacob SW. Angew. Chem. Int. Ed. 1999, 38: 3160 1e Hanessian S. Yang R.-Y. Tetrahedron Lett. 1996, 37: 5273 1f Miyabe H. Yamaoka Y. Naito T. Takemoto Y. J. Org. Chem. 2003, 68: 6745 1g Dieter RK. Datar R. Can. J. Chem. 1993, 71: 814 For some examples of radical addition to oxime ethers, see: 2a Miyabe H. Ueda M. Nishimura A. Naito T. Org. Lett. 2002, 4: 131 2b Miyabe H. Ushiro C. Ueda M. Yamakawa K. Naito T. J. Org. Chem. 2000, 65: 176 2c Miyabe H. Fujii K. Naito T. Org. Lett. 1999, 1: 569 2d Miyabe H. Shibata R. Ushiro C. Naito T. Tetrahedron Lett. 1998, 39: 631 2e Hart DJ. Seely FL. J. Am. Chem. Soc. 1988, 110: 1631 3a Bull SD. Davies SG. Domingez SH. Jones S. Price AJ. Sellers TGR. Thomas GR. Smith AD. J. Chem. Soc., Perkin Trans. 1 2002, 2141 3b Davies SG. Fox JF. Jones S. Price AJ. Sanz MA. Sellers TGR. Smith AD. Teixeira FC. J. Chem. Soc., Perkin Trans. 1 2002, 1757 3c Koenig SG. Leonard KA. Lowe RS. Austin DJ. Tetrahedron Lett. 2000, 41: 9393 4 Baker R. Nobbs MS. Tetrahedron Lett. 1977, 3759 As a related study, the palladium-catalyzed deprotection of O-allyl oxime ethers and its application were reported. See: 5a Yamada T. Goto K. Mitsuda Y. Tsuji J. Tetrahedron Lett. 1987, 28: 4557 5b Suzuki O. Hashiguchi Y. Inoue S. Sato K. Chem. Lett. 1988, 291 6 Miyabe H. Yoshida K. Matsumura A. Yamauchi M. Takemoto Y. Synlett 2003, 567 7 The equilibrium acidities of oximes have been measured in DMSO. The pKHA values for bezaldoxime 1A and cyclo-hexanone oxime 1C were 20.2 and 24.3, respectively. See: Bordwell FG. Ji G.-Z. J. Org. Chem. 1992, 57: 3019 8a Takeuchi R. Ue N. Tanabe K. Yamashita K. Shiga N. J. Am. Chem. Soc. 2001, 123: 9525 8b Takeuchi R. Ue N. Tanabe K. Angew. Chem. Int. Ed. 2000, 39: 1975 8c Takeuchi R. Shiga N. Org. Lett. 1999, 1: 265 8d Takeuchi R. Kashio M. J. Am. Chem. Soc. 1998, 120: 8647 8e Takeuchi R. Kashio M. Angew. Chem., Int. Ed. Engl. 1997, 36: 263 8f For a review, see: Takeuchi R. Synlett 2002, 1954 For some related examples, see: 9a Bartels B. Helmchen G. Chem. Commun. 1999, 741 9b Fuji K. Kinoshita N. Tanaka K. Kawabata T. Chem. Commun. 1999, 2289 9c Ohmura T. Hartwig JF. J. Am. Chem. Soc. 2002, 124: 15164 9d Lipowsky G. Helmchen G. Chem. Commun. 2004, 116 9e Nakagawa H. Hirabayashi T. Sakaguchi S. Ishii Y. J. Org. Chem. 2004, 69: 3474 Our studies on the iridium-catalyzed reaction. See: 10a Kanayama T. Yoshida K. Miyabe H. Takemoto Y. Angew. Chem. Int. Ed. 2003, 42: 2054 10b Kanayama T. Yoshida K. Miyabe H. Kimachi Y. Takemoto Y. J. Org. Chem. 2003, 68: 6197 10c Miyabe H. Yoshida K. Kobayashi Y. Matsumura A. Takemoto Y. Synlett 2003, 1031 11 Kim H. Lee C. Org. Lett. 2002, 4: 4369 12a Kimura M. Tomozawa T. Horino Y. Tanaka S. Tamaru Y. Tetrahedron Lett. 2000, 41: 3627 12b Kimura M. Horino Y. Mukai R. Tanaka S. Tamaru Y. J. Am. Chem. Soc. 2001, 123: 10401
