Diastereoselective and enantioselective Rh(I)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines

Journal of the American Chemical Society

Volumn 127, Issue 4, 2005, Pages 1092-1093

  Weix, Daniel J ^a   Shi, Yili ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLBORONIC ACID; BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; IMINE; N TERT BUTANESULFINYL; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; GRIGNARD REACTION; PROTON TRANSPORT; STEREOCHEMISTRY; STOICHIOMETRY;

ALDEHYDES; AMINES; BORONIC ACIDS; CATALYSIS; IMINES; PHOSPHINIC ACIDS; RHODIUM; STEREOISOMERISM; SULFINIC ACIDS;

EID: 13644262210     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044003d     Document Type: Article

References (34)

1. (a) Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
2. (b) Côté, A.; Boezio, A. A.; Charette, A. B. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5405-5511.
3. (c) Hermanns, N.; Dahmen, S.; Bolm, C.; Bräse, S. Angew. Chem., Int. Ed. 2002, 41, 3692-3694.
4. (d) Akullian, L. C.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4244-4247.
5. (e) Li, S.-W.; Batey, R. Chem. Commun. 2004, 1382-1383.
6. (a) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
7. (b) Pflum, D. A.; Krishnamurthy, D.; Han, Z.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2002, 43, 923-926.
8. (c) Plobeck, N.; Powell, D. Tetrahedron: Asymmetry 2002, 13, 303-310.
9. (d) Han, Z.; Krishnamurthy, D.; Grover, P.; Fang, Q. K.; Pflum, D. A.; Senanayake, C. H. Tetrahedron Lett. 2003, 44, 4195-4197.
10. (e) Kells, K. W.; Chong, J. M. Org. Lett. 2003, 5, 4215-4218.
11. (f) Cooper, I. R.; Grigg, R.; Hardie, M. J.; MacLachlan, W. S.; Sridharan, V.; Thomas, W. A. Tetrahedron Lett. 2003, 44, 2283-2285.
12. (g) Rech, J. R.; Floreancig, P. E. Org. Lett. 2003, 5, 1495-1498.
13. (h) Jung, P. M.; Beaudegnies, R.; De Mesmaeker, A.; Wendeborn, S. Tetrahedron Lett. 2003, 44, 293-297.
14. (i) Chemla, F.; Ferreira, F. Synlett 2004, 983-986.
15. (j) Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock M. G. Tetrahedron Lett. 2004, 45, 6641-6643.
16. (k) Jayathilaka, L. P.; Deb, M.; Standaert, R. F. Org. Lett. 2004, 6, 3659-3662.
17. For functionalized Grignard reagents, see: (a) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320. For functionalized lithium reagents, see: (b) Nájera, C.; Yus, M. Curr. Org. Chem. 2003, 7, 867-926.
18. For functionalized Grignard reagents, see: (a) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320. For functionalized lithium reagents, see: (b) Nájera, C.; Yus, M. Curr. Org. Chem. 2003, 7, 867-926.
19. (a) Ueda, M.; Saito, A.; Miyaura, N. Synlett 2000, 1637-1639.
20. (b) Kuriyama, M.; Soeta, T.; Hao, X.; Chen, Q.; Tomioka. K. J. Am. Chem. Soc. 2004, 8128-8129.
21. (c) Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584-13585.
22. Rhodium-catalyzed additions of arylboronic acids to aldehydes and α,β-unsaturated ketones proceed with a high level of functional group compatibility, (a) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169-196.
23. Rhodium-catalyzed additions of arylboronic acids to aldehydes and α,β-unsaturated ketones proceed with a high level of functional group compatibility, (a) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169-196.
24. (a) Ramage, R.; Hopton, D.; Parrott, M.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1 1984, 1357-1370.
25. (b) Osborn, H. M. I.; Sweeney, J. B. Synlett 1994, 145-147.
26. (c) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364-7375.
27. See Supporting Information for details and complete tables of results.
28. (a) Kiem, W. J. Organomet. Chem. 1968, 14, 179-184.
29. (b) Boyd, S. E.; Field, L. D.; Hambley, T. W.; Partridge, M. G. Organometallics 1993, 12, 1720-1724.
30. 3N complexes, which may transmetalate more rapidly. See: McKinley, N. F.; O'Shea, D. F. J. Org. Chem. 2004, 69, 5088-5090.
31. 1 = 2-phenylethyl).
32. Other ligands screened gave very low conversions; for example, PHA-NEPHOS, DIOP, QUINAP, JOSIPHOS, WALPHOS, MANDYPHOS, i-Pr-PHOX, Me-BPE.
33. This ligand is available as "catASium D(R)" from Strem Chemicals, Inc. and ACBR, GmbH. Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Chem. Ber. 1986, 119, 3326-2243.
34. Quantities of 3.6 (ref 4c) to 5.0 (ref 4b) equiv of arylboronic acid are generally used with N-toluenesulfonyl imine substrates in similar reactions.