Chiral diaminophosphine ligands with stable C(aryl)-N(amine) axial chirality derived from prolinol

Tetrahedron Letters

Volumn 44, Issue 25, 2003, Pages 4677-4679

  Mino, Takashi ^a   Tanaka, Youichi ^a   Sato, Yutaka ^a   Saito, Akio ^a   Sakamoto, Masami ^a   Fujita, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Asymmetric allylic alkylation; C N axial chirality; P,N ligand; Palladium

Indexed keywords

1,3 DIPHENYL 2 PROPENYL ACETATE; ACETIC ACID DERIVATIVE; AMINOPHOSPHINE OXIDE; MALONIC ACID DERIVATIVE; PALLADIUM; PHOSPHINE DERIVATIVE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE;

EID: 0038101603     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01097-9     Document Type: Article

References (29)

1. Tsuji J., Minami I. Acc. Chem. Res. 20:1987;140.
2. Trost B.M., Verhoeven T.R. Wilkinson G., Stone F.G.A., Abel E.W. Comprehensive Organometallic Chemistry. 8:1982;799 Pergamon, Oxford.
3. Trost B.M. Acc. Chem. Res. 13:1980;385.
4. Trost B.M. Chem. Pharm. Bull. 50:2002;1.
5. Trost B.M., Lee C. Ojima I. Catalytic Asymmetric Synthesis. 2nd ed. 2000;893 VCH Publishers, New York.
6. Helmchen G. J. Organomet. Chem. 576:1999;203.
7. Pfaltz A., Lautens M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. 2:1999;833 Springer, Tokyo. and references cited therein.
8. Dawson J.G., Frost C.G., Williams J.M.J., Coote S.J. Tetrahedron Lett. 34:1993;3149.
9. Von Matt P., Pfaltz A. Angew. Chem., Int. Ed. Engl. 32:1993;566.
10. Sprinz J., Helmchen G. Tetrahedron Lett. 34:1993;1769.
11. Hattori T., Komuro Y., Hashizaka N., Takahashi H., Miyano S. Enantiomer. 2:1997;203.
12. Mino T., Tanaka Y., Sakamoto M., Fujita T. Heterocycles. 53:2000;1485.
13. Mino T., Tanaka Y., Akita K., Anada K., Sakamoto M., Fujita T. Tetrahedron: Asymmetry. 12:2001;1677.
14. Kondo K., Kazuta K., Fujita H., Sakamoto Y., Murakami Y. Tetrahedron. 58:2002;5209.
15. Mino T., Tanaka Y., Sakamoto M., Fujita T. Tetrahedron: Asymmetry. 12:2001;2435.
16. Mino T., Tanaka Y., Akita K., Sakamoto M., Fujita T. Heterocycles. 60:2003;9.
17. For other pyrrolidine-containing aminophosphine ligands, see: (a) Farrell, A.; Goddard, R.; Guiry, P. J. J. Org. Chem. 2002, 67, 4209; (b) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193; (c) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89; (d) Hiroi, K.; Suzuki, Y.; Abe, I. Tetrahedron: Asymmetry 1999, 10, 1173; (e) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157.
18. For other pyrrolidine-containing aminophosphine ligands, see: (a) Farrell, A.; Goddard, R.; Guiry, P. J. J. Org. Chem. 2002, 67, 4209; (b) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193; (c) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89; (d) Hiroi, K.; Suzuki, Y.; Abe, I. Tetrahedron: Asymmetry 1999, 10, 1173; (e) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157.
19. For other pyrrolidine-containing aminophosphine ligands, see: (a) Farrell, A.; Goddard, R.; Guiry, P. J. J. Org. Chem. 2002, 67, 4209; (b) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193; (c) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89; (d) Hiroi, K.; Suzuki, Y.; Abe, I. Tetrahedron: Asymmetry 1999, 10, 1173; (e) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157.
20. For other pyrrolidine-containing aminophosphine ligands, see: (a) Farrell, A.; Goddard, R.; Guiry, P. J. J. Org. Chem. 2002, 67, 4209; (b) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193; (c) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89; (d) Hiroi, K.; Suzuki, Y.; Abe, I. Tetrahedron: Asymmetry 1999, 10, 1173; (e) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157.
21. For other pyrrolidine-containing aminophosphine ligands, see: (a) Farrell, A.; Goddard, R.; Guiry, P. J. J. Org. Chem. 2002, 67, 4209; (b) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193; (c) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89; (d) Hiroi, K.; Suzuki, Y.; Abe, I. Tetrahedron: Asymmetry 1999, 10, 1173; (e) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157.
22. Rate of (aS,S)-3a / (aR,S)-3a was ca. 2.3 determined by NMR.
23. Rate of (aS,S)-3b / (aR,S)-3b was ca. 2.5 determined by NMR.
24. Rate of (aS,S)-3c / (aR,S)-3c was ca. 2.0 determined by NMR.
25. 2OP+H 445.2409, found 445.2369.
26. Rate of (aS,S)-3e/(aR,S)-3e was ca. 1.8 determined by NMR.
27. Mino T., Imiya W., Yamashita M. Synlett. 1997;583.
28. Mino T., Shiotsuki M., Yamamoto N., Suenaga T., Sakamoto M., Fujita T., Yamashita M. J. Org. Chem. 66:2001;1795.
29. Rate of (aS,S)-3d/(aR,S)-3d was ca. 1.4 determined by NMR.