Novel chiral xylofuranose-based phosphinooxathiane and phosphinooxazinane ligands for palladium-catalyzed asymmetric tandem allylic allylation

Tetrahedron Letters

Volumn 43, Issue 43, 2002, Pages 7761-7764

  Nakano, Hiroto ^a   Yokoyama, Jun Ichi ^a   Fujita, Reiko ^a   Hongo, Hiroshi ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

asymmetric tandem allylic allylation; Palladium; Phosphinooxathiane; Phosphinooxazinane

Indexed keywords

1,2 BIS(BENZYLAMINO)ETHANE; 1,4 DIACETOXY 2 BUTENE; 1,4 DIBENZYL 2 VINYLPIPERAZINE; 2 (BENZYLAMINO)ETHANOL]; 4 BENZYL 2 VINYLMORPHOLINE; ALCOHOL; ALLYL COMPOUND; BUTANE; ETHANE; FURAN DERIVATIVE; MORPHOLINE DERIVATIVE; OXATHIIN DERIVATIVE; OXAZINE DERIVATIVE; PALLADIUM; PHOSPHINOOXATHIANE; PHOSPHINOOXAZINANE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG; XYLOFURANOSE;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHIRALITY; SYNTHESIS;

EID: 0037152333     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01830-0     Document Type: Article

References (28)

1. For recent reviews including palladium-catalyzed allylic substitution reactions; see: (a) Tsuji, J. Palladium Reagents and Catalysis; Innovations in Organic Synthesis; Wiley: New York, 1995; (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (c) Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689-1708; (d) Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202; (e) Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
2. For recent reviews including palladium-catalyzed allylic substitution reactions; see: (a) Tsuji, J. Palladium Reagents and Catalysis; Innovations in Organic Synthesis; Wiley: New York, 1995; (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (c) Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689-1708; (d) Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202; (e) Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
3. For recent reviews including palladium-catalyzed allylic substitution reactions; see: (a) Tsuji, J. Palladium Reagents and Catalysis; Innovations in Organic Synthesis; Wiley: New York, 1995; (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (c) Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689-1708; (d) Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202; (e) Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
4. For recent reviews including palladium-catalyzed allylic substitution reactions; see: (a) Tsuji, J. Palladium Reagents and Catalysis; Innovations in Organic Synthesis; Wiley: New York, 1995; (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (c) Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689-1708; (d) Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202; (e) Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
5. For recent reviews including palladium-catalyzed allylic substitution reactions; see: (a) Tsuji, J. Palladium Reagents and Catalysis; Innovations in Organic Synthesis; Wiley: New York, 1995; (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (c) Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689-1708; (d) Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202; (e) Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
6. Janssen J.P., Helmchen G. Tetrahedron Lett. 38:1997;8025.
7. Hayashi T., Kawatsura M., Uozumi Y. J. Am. Chem. Soc. 120:1998;1681-1687.
8. Pretot R., Pfaltz A. Angew. Chem., Int. Ed. Engl. 37:1998;323-325.
9. Yonehara K., Hashizume T., Mori K., Uemura S. J. Org. Chem. 64:1999;9374-9380.
10. Deng W.-P., Hou X.-L., Dai L.-X., Yu Y.-H., Xia W. Chem. Commun. 2000;285-286.
11. Fuji K., Ohnishi H., Moriyama S., Tanaka K., Kawabata T., Tsubaki K. Synlett. 12:2000;351-352.
12. Mino T., Hata S., Ohtaka K., Sakamoto M., Fujita T. Tetrahedron Lett. 42:2001;4837-4839.
13. Stranne R., Vasse J.-L., Moberg C. Org. Lett. 3:2001;2525-2528.
14. Dai W.-M., Yeung K.K.Y., Liu J.-T., Zhang Y., Williams I.D. Org. Lett. 4:2002;1615-1618.
15. Tsuda T., Kiyoi T., Saegusa T. J. Org. Chem. 55:1990;3388-3390.
16. Morie T., Kato S., Harada H., Yoshida N., Matsumoto J. Chem. Pharm. Bull. 42:1994;877-882.
17. Sakurai N., Sano M., Hirayama F., Kuroda T., Uemori S., Moriguchi A., Yamamoto K., Ikeda Y., Kawakita T. Bioorg. Med. Lett. 8:1998;2185-2190.
18. Berg S., Larsson L.-G., Renyi L., Ross S.B., Thorberg S.-O., Thorell-Svantesson G. J. Med. Chem. 41:1998;1934-1942.
19. Dorsey B.D., McDonough C., McDaniel S.L., Levin R.B.L., Newton C.L., Hoffman J.M., Darke P.L., Zugay-Murphy J.A., Emilio E.A., Schleif W.A., Olsen D.B., Stahlhut M.W., Rutkowski C.A., Kuo L.C., Lin J.H., Chen I.-W., Michelson S.R., Holloway M.K., Huff J.R., Vacca J.P. J. Med. Chem. 43:2000;3386-3399.
20. Uozumi Y., Tanahashi A., Hayashi T. J. Org. Chem. 58:1993;6826-6832.
21. Yamazaki A., Achiwa K. Tetrahedron: Asynmmetry. 5:1995;1021-1024.
22. For norbornane-based phosphinooxathiane ligand 13, see: (a) Nakano, H.; Okuyama, Y.; Hongo, H. Tetrahedron Lett. 2000, 41, 4615-4618; (b) Nakano, H.; Okuyama, Y.; Yanagida, M.; Hongo, H. J. Org. Chem. 2001, 66, 620-625; (c) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014.
23. For norbornane-based phosphinooxathiane ligand 13, see: (a) Nakano, H.; Okuyama, Y.; Hongo, H. Tetrahedron Lett. 2000, 41, 4615-4618; (b) Nakano, H.; Okuyama, Y.; Yanagida, M.; Hongo, H. J. Org. Chem. 2001, 66, 620-625; (c) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014.
24. For norbornane-based phosphinooxathiane ligand 13, see: (a) Nakano, H.; Okuyama, Y.; Hongo, H. Tetrahedron Lett. 2000, 41, 4615-4618; (b) Nakano, H.; Okuyama, Y.; Yanagida, M.; Hongo, H. J. Org. Chem. 2001, 66, 620-625; (c) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014.
25. For pyrrolidine-based phosphinooxazolidine ligand 14, see: (d) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11. 1193-1198; (e) Nakano, H.; Okuyama, Y.; Suzuki, Y.; Fujita, Y.; Kabuto, C. Chem. Commun. 2002, 1146-1147.
26. For pyrrolidine-based phosphinooxazolidine ligand 14, see: (d) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11. 1193-1198; (e) Nakano, H.; Okuyama, Y.; Suzuki, Y.; Fujita, Y.; Kabuto, C. Chem. Commun. 2002, 1146-1147.
27. +): 565.2382.
28. 2 (2.7 mg, 0.004 mmol) in dry dichloromethane (3 ml) was strried at rt. After 1 h, triethylamine (0.080 ml, 0.58 mmol), 10a (0.050 ml, 0.29 mmol), and 11a (44 mg, 0.29 mmol) were added at 0°C and was stirred for 72 h. The solvent was evaporated under reduced pressure and the residue was purified by preparative TLC (hexane/AcOEt=5/1) to give a pure product 12a (35.6 mg, 60%). The enantiomeric excess was determined by HPLC (Chiralcel OD-H, 0.5 ml/min, hexane/2-propanol=59/1, S-12a: 10.3 min, R-12b: 11.0 min).