Preparation of 2-amino-2'-hydroxy-1,1'-binaphthyl and N-arylated 2- amino-1,1'-binaphthyl derivatives via palladium-catalyzed amination

Tetrahedron Letters

Volumn 40, Issue 6, 1999, Pages 1095-1098

  Singer, Robert A ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1,1' BINAPHTHYL DERIVATIVE; 2 AMINO 2' HYDROXY 1,1' BINAPHTHYL DERIVATIVE; NAPHTHYL GROUP; PALLADIUM; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; SYNTHESIS;

EID: 0033524686     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02642-2     Document Type: Article

References (26)

1. (1) (a) Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517.
2. (b) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley & Sons: New York, 1994.
3. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994.
4. (2) (a) Smrcina, M.; Lorenc, M.; Hanus, V.; Kocovsky, P. Synlett 1991, 231-232.
5. (b) Smrcina, M.; Vyskocil, S.; Polívková, J.; Poláková, J.; Kocovsky, P. Collect. Czech. Chem. Commun. 1996, 61, 1520-1524.
6. (3) Vyskocil, S.; Jaracz, S.; Smrcina, M.; Stícha, M.; Hanus, V.; Polásek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7727-7737.
7. (4) (a) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837-8838.
8. (b) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649-3650.
9. (c) Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360-12361.
10. (d) Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927-930.
11. (5) (a) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
12. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
13. (c) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2047-2067.
14. (d) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res., in press.
15. (6) We found it more effective to prepare benzophenone imine by treatment of bromobenzene with n-butyllithium at -78 °C in THF for 45 min followed by addition of benzonitrile and warming to rt, rather than the conventional method of using the Grignard reagent
16. (7) DPPF gave the best results, affording product in 35% yield after 48 h at 110 °C.
17. (8) The 4-methoxybenzyl (PMB) protecting group was chosen for its high lability to hydrogenolysis and for improving the solubility properties of the imine product. If the benzyl group was substituted for a methyl protecting group, the imine product was found to be highly insoluble in most organic solvents.
18. 3) δ 158.9, 154.2, 145.5, 133.5, 132.4, 130.8, 130.0, 129.0, 128.9, 128.1, 128.0, 127.9, 127.2, 127.2, 126.9, 126.6, 125.0, 124.6, 123.8, 120.3, 119.4, 116.1, 114.8, 113.6, 109.2, 70.6, 55.2.
19. (10) Sadighi, J. P.; Harris, M. C.; Buchwald, S. L. Tetrahedron Lett. 1998, 39, 5327-5330.
20. 2. The reactions were typically conducted at 1 M with respect to 5. Diluting the reactions further led to significantly slower rates of reaction.
21. 3) δ 159.0, 154.4, 142.1, 134.2, 133.7, 129.9, 129.7, 129.4, 129.0, 128.7, 128.2, 128.0, 127.9, 126.8, 126.2, 125.2, 124.4, 124.2, 122.1, 120.7, 118.2, 117.1, 113.8, 113.6, 71.3, 55.2.
22. 2).
23. (14) The optical purity of 1 was assayed by HPLC using a chiralcel OD column. For a flow rate of 0.5 mL/min and eluent composition of 80% i-PrOH and 20% hexane, 1 eluted at 22.7 min and ent-I eluted at 20.8 min.
24. 3) δ 167.3, 158.7, 154.1, 147.1, 143.9, 137.3, 134.2, 133.8, 133.3, 131.3, 130.6, 129.6, 129.4, 129.2. 128.2, 127.8, 127.8, 126.4, 126.1, 125.8, 125.1, 125.0, 124.2, 123.6, 122.2, 119.9, 116.9, 115.4, 114.4, 113.4, 113.0, 70.6, 60.2, 55.1, 14.2.
25. (16) Compounds 5-11 gave satisfactory elemental analysis.
26. (17) We have recently purchased optically pure BINOL from Environmental Science Center Limited, Yokohama, Japan for under $3/g.