Synthesis, Inhaltsverzeichnis SPECIALTOPIC© Georg Thieme Verlag Stuttgart · New YorkP-Chirogenic Phosphine/Sulfide Hybrid LigandsHiroshi Sugama, Hirohisa Saito, Hiroshi Danjo, Tsuneo Imamoto*Department of Chemistry, Faculty of Science, Chiba University, Inage-ku, Chiba 263-8522, JapanFax: +81(43)2902791; e-Mail: imamoto@scichem.s.chiba-u.ac.jp; Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract P-Chirogenic phosphine/sulfide hybrid ligands 1 were prepared by the use of optically active phosphine-boranes as the intermediates. The palladium complexes of the ligands exhibited high catalytic activity and enantioselectivity in allylic alkylation of 1-acetoxy-1,3-diphenylprop-2-ene with malonate esters. Key words asymmetric catalysis - allylation - palladium - phosphorus - sulfur Volltext Referenzen References For reviews, see: <A NAME="RC04201SS-1A">1a</A> Kagan HB. In Asymmetric Synthesis Vol. 5: Morrison JD. Academic Press; Orland: 1985. Chap. 1. <A NAME="RC04201SS-1B">1b</A> Noyori R. In Asymmetric Catalysis in Organic Synthesis Wiley; New York: 1994. <A NAME="RC04201SS-1C">1c</A> Jacobsen EN. Pfaltz A. Yamamoto H. In Comprehensive Asymmetric Catalysis Springer; Berlin: 1999. <A NAME="RC04201SS-1D">1d</A> Catalytic Asymmetric Synthesis Ojima I. VCH; Wheinheim: 2000. p.2nd ed; For examples, see: <A NAME="RC04201SS-2A">2a</A> Kagan HB. Dang T.-P. J. Am. Chem. Soc. 1972, 94: 6429 <A NAME="RC04201SS-2B">2b</A> Vineyard BD. Knowles WS. Sabacky SJ. Bachman GL. Weinkauff DJ. J. Am. Chem. Soc. 1977, 99: 5946 <A NAME="RC04201SS-2C">2c</A> Miyashita A. Yasuda A. Takaya H. Toriumi K. Ito T. Souchi T. Noyori R. J. Am. Chem. Soc. 1980, 102: 7932 <A NAME="RC04201SS-2D">2d</A> Burk MJ. J. Am. Chem. Soc. 1991, 113: 8518 <A NAME="RC04201SS-2E">2e</A> Burk MJ. Angew. Chem., Int. Ed. 1998, 37: 1931 <A NAME="RC04201SS-2F">2f</A> Robin F., Mercier F., Richard L., Mathey F., Spagnol M.; Chem. Eur. J.; 1997, 3: 1365 <A NAME="RC04201SS-2G">2g</A> Jiang Q. Jiang Y. Xiao D. Cao P. Zhang X. Angew. Chem., Int. Ed. 1998, 37: 1100 For recent examples, see: <A NAME="RC04201SS-3A">3a</A> Hayashi T. Yamamoto A. Hojo M. Ito Y. Chem. Commun. 1989, 495 <A NAME="RC04201SS-3B">3b</A> Yoshikawa K. Yamamoto N. Murata M. Awano K. Morimoto T. Achiwa K. Tetrahedron: Asymmetry 1992, 3: 13 <A NAME="RC04201SS-3C">3c</A> Togni A. Breutel C. Schnyder A. Spindler F. Landert H. Tijani A. J. Am. Chem. Soc. 1994, 116: 4062 <A NAME="RC04201SS-3D">3d</A> Nozaki K. Sato N. Takaya H. J. Am. Chem. Soc. 1995, 117: 9911 <A NAME="RC04201SS-3E">3e</A> Carmichael D. Doucet H. Brown MJ. Chem. Commun. 1999, 261 For recent examples of P/S hybrid ligands, see: <A NAME="RC04201SS-4A">4a</A> Togni A. Häusel R. Synlett 1990, 633 <A NAME="RC04201SS-4B">4b</A> Hiraoka M. Nishikawa A. Morimoto T. Achiwa K. Chem. Pharm. Bull. 1998, 46: 704 <A NAME="RC04201SS-4C">4c</A> Enders D. Peters R. Runsink J. Bats JW. Org. Lett. 1999, 1: 1863 <A NAME="RC04201SS-4D">4d</A> Evans DA. Campos KR. Tedrow JS. Michael EF. Gagné MR. J. Am. Chem. Soc. 2000, 122: 7905 <A NAME="RC04201SS-4E">4e</A> Nakano H. Okuyama Y. Yanagida M. Hongo H. J. Org. Chem. 2001, 66: 620 For recent examples of P/N hybrid ligands, see: <A NAME="RC04201SS-5A">5a</A> Allen JV. Coote SJ. Dawson GJ. Frost CG. Martin CJ. Williams JMJ. J. Chem. Soc., Perkin Trans. 1 1994, 2065 <A NAME="RC04201SS-5B">5b</A> Lightfoot A. Schnider P. Pfaltz A. Angew. Chem., Int. Ed. 1998, 37: 2897 <A NAME="RC04201SS-5C">5c</A> Flubacher D. Helmchen G. Tetrahedron Lett. 1999, 40: 3867 <A NAME="RC04201SS-5D">5d</A> Gilbertson SR. Fu Z. Xie D. Tetrahedron Lett. 2001, 42: 365 <A NAME="RC04201SS-5E">5e</A> Uozumi Y. Shibatomi K. J. Am. Chem. Soc. 2001, 123: 2919 <A NAME="RC04201SS-6">6</A> Imamoto T. Watanabe J. Wada Y. Masuda H. Yamada H. Tsuruta H. Matsukawa S. Yamaguchi K. J. Am. Chem. Soc. 1998, 120: 1635 <A NAME="RC04201SS-7">7</A> Yamanoi Y. Imamoto T. J. Org. Chem. 1999, 64: 2988 <A NAME="RC04201SS-8A">8a</A> Ohashi A. Imamoto T. Tetrahedron Lett. 2001, 42: 1099 <A NAME="RC04201SS-8B">8b</A> Ohashi A. Imamoto T. Org. Lett. 2001, 3: 373 For general reviews, see: <A NAME="RC04201SS-9A">9a</A> Trost BM. Van Vranken DL. Chem. Rev. 1996, 96: 395 ; and references cited therein <A NAME="RC04201SS-9B">9b</A> Hayashi T. In Catalytic Asymmetric Synthesis Ojima I. VCH; New York: 1993. p.325 <A NAME="RC04201SS-9C">9c</A> Consiglio G. Waymouth RM. Chem. Rev. 1989, 89: 257 <A NAME="RC04201SS-10">10</A> Nagata K. Matsukawa S. Imamoto T. J. Org. Chem. 2000, 65: 4185 <A NAME="RC04201SS-11">11</A> Muci AR. Campos KR. Evans DA. J. Am. Chem. Soc. 1995, 117: 9075 <A NAME="RC04201SS-12">12</A> McKinstry L. Livinghouse T. Tetrahedron Lett. 1994, 35: 9319 <A NAME="RC04201SS-13">13</A> Imamoto T. Oshiki T. Onozawa T. Kusumoto T. Sato K. J. Am. Chem. Soc. 1990, 112: 5244