Stereoselective Synthesis of (E)- and (Z)-Allylphosphonium Salts by Palladium-Catalyzed Addition of Phosphine to Allene

Advanced Synthesis and Catalysis

Volumn 343, Issue 1, 2001, Pages 27-28

  Arisawa, Mieko ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

(E) allylphosphonium salt; (Z) allylphosphonium salt; Allene; Palladium; Phosphine

Indexed keywords

EID: 0002194392     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010129)343:1<27::AID-ADSC27>3.0.CO;2-U     Document Type: Article

References (11)

1. S. E. Kelly, Alkene Synthesis. In: Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press: New York, 1991; Chapter 3.1, Vol. 1, p 729.
2. R. Tamura, M. Kato, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1987, 52, 4121-1124; Y. Tsukahara, H. Kinoshita, K. Inomata, H. Kotake, Bull. Chem. Soc. Jpn. 1984, 57, 3013-3014; Y. Inoue, M. Toyofuku, H. Hashimoto, Bull. Chem. Soc. Jpn. 1986, 59, 1279-1280; M. Moreno-Mañas, A. Trius, Bull. Chem. Soc. Jpn. 1983, 56, 2154-2158.
3. R. Tamura, M. Kato, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1987, 52, 4121-1124; Y. Tsukahara, H. Kinoshita, K. Inomata, H. Kotake, Bull. Chem. Soc. Jpn. 1984, 57, 3013-3014; Y. Inoue, M. Toyofuku, H. Hashimoto, Bull. Chem. Soc. Jpn. 1986, 59, 1279-1280; M. Moreno-Mañas, A. Trius, Bull. Chem. Soc. Jpn. 1983, 56, 2154-2158.
4. R. Tamura, M. Kato, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1987, 52, 4121-1124; Y. Tsukahara, H. Kinoshita, K. Inomata, H. Kotake, Bull. Chem. Soc. Jpn. 1984, 57, 3013-3014; Y. Inoue, M. Toyofuku, H. Hashimoto, Bull. Chem. Soc. Jpn. 1986, 59, 1279-1280; M. Moreno-Mañas, A. Trius, Bull. Chem. Soc. Jpn. 1983, 56, 2154-2158.
5. R. Tamura, M. Kato, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1987, 52, 4121-1124; Y. Tsukahara, H. Kinoshita, K. Inomata, H. Kotake, Bull. Chem. Soc. Jpn. 1984, 57, 3013-3014; Y. Inoue, M. Toyofuku, H. Hashimoto, Bull. Chem. Soc. Jpn. 1986, 59, 1279-1280; M. Moreno-Mañas, A. Trius, Bull. Chem. Soc. Jpn. 1983, 56, 2154-2158.
6. M. Arisawa, M. Yamaguchi, J. Am. Chem. Soc. 2000, 122, 2387-2388.
7. Such (Z)-selectivity in the Pd-catalyzed addition reactions of allene is known; M. Ahmar, J.-J. Barieux, B. Cazes, J. Gore, Tetrahedron 1987, 43, 515-526; B. Cazes, Pure Appl. Chem. 1990, 62, 1867-1878.
8. Such (Z)-selectivity in the Pd-catalyzed addition reactions of allene is known; M. Ahmar, J.-J. Barieux, B. Cazes, J. Gore, Tetrahedron 1987, 43, 515-526; B. Cazes, Pure Appl. Chem. 1990, 62, 1867-1878.
9. For some exceptions using sophisticated (E)-allylphosphonium salts, see: R. Ideses, A. Shani, Tetrahedron 1989, 45, 3523-3534; R. Tamura, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1988, 53, 2723-2728; Q. Wang, M. E. Khoury, M. Schlosser, Chem. Eur. J. 2000, 6, 420-426.
10. For some exceptions using sophisticated (E)-allylphosphonium salts, see: R. Ideses, A. Shani, Tetrahedron 1989, 45, 3523-3534; R. Tamura, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1988, 53, 2723-2728; Q. Wang, M. E. Khoury, M. Schlosser, Chem. Eur. J. 2000, 6, 420-426.
11. For some exceptions using sophisticated (E)-allylphosphonium salts, see: R. Ideses, A. Shani, Tetrahedron 1989, 45, 3523-3534; R. Tamura, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1988, 53, 2723-2728; Q. Wang, M. E. Khoury, M. Schlosser, Chem. Eur. J. 2000, 6, 420-426.