Regio- and enantioselective intermolecular hydroacylation: Substrate-directed addition of salicylaldehydes to homoallylic sulfides

Journal of the American Chemical Society

Volumn 132, Issue 46, 2010, Pages 16330-16333

  Coulter, Matthew M ^a   Kou, Kevin G M ^a   Galligan, Baye ^a   Dong, Vy M ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE; HYDROACYLATION; PHOSPHORAMIDITE LIGANDS; SALICYLALDEHYDE; SUBSTRATE-BOUND;

ALDEHYDES; KETONES; RHODIUM;

OLEFINS;

ALKENE; KETONE DERIVATIVE; SALICYLALDEHYDE; SPIRO COMPOUND;

ACYLATION; ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; SUBSTITUTION REACTION; SYNTHESIS;

ACYLATION; ALDEHYDES; ALLYL COMPOUNDS; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFIDES;

EID: 78649927355     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107198e     Document Type: Article

References (46)

1. Willis, M. C. Chem. Rev. 2010, 110, 725
2. Barnhart, R. W., Wang, X., Noheda, P., Bergens, S. H., Whelan, J., and Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821
3. Kundu, K., McCullagh, J. V., and Morehead, A. T., Jr. J. Am. Chem. Soc. 2005, 127, 16042
4. Coulter, M. M., Dornan, P. K., and Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932 and references therein
5. Stemmler, R. T. and Bolm, C. Adv. Synth. Catal. 2007, 349, 1185
6. Phan, D. H. T., Kou, K. G. M., and Dong, V. M. J. Am. Chem. Soc. 2010, doi: 10.1021/ja107738a.
7. Osborne, J. D., Randell-Sly, H. E., Currie, G. S., Cowley, A. R., and Willis, M. C. J. Am. Chem. Soc. 2008, 130, 17232
8. Shibata, Y. and Tanaka, K. J. Am. Chem. Soc. 2009, 131, 12552
9. For a definition of simple olefins as those not belonging to strained or conjugated systems, see
10. Tsui, G. C., Menard, F., and Lautens, M. Org. Lett. 2010, 12, 2456
11. Inui, Y., Tanaka, M., Imai, M., Tanaka, K., and Suemune, H. Chem. Pharm. Bull. 2009, 57, 1158
12. Jun, C.-H., Lee, D.-Y., Lee, H., and Hong, J.-B. Angew. Chem., Int. Ed. 2000, 39, 3070
13. Willis, M. C., McNally, S. J., and Beswick, P. J. Angew. Chem., Int. Ed. 2004, 43, 340
14. Roy, A. H., Lenges, C. P., and Brookhart, M. J. Am. Chem. Soc. 2007, 129, 2082
15. For examples of Rh-catalyzed, branch-selective intermolecular hydroacylation with dienes, see
16. Imai, M., Tanaka, M., Tanaka, K., Yamamoto, Y., Imai-Ogata, N., Shimowatari, M., Nagumo, S., Kawahara, N., and Suemune, H. J. Org. Chem. 2004, 69, 1144 With anhydrides and styrene derivatives, see: Hong, Y.-T., Barchuk, A., and Krische, M. J. Angew. Chem., Int. Ed. 2006, 45, 6885
17. Miura developed the use of salicylaldehyde in intermolecular alkyne hydroacylation; see
18. Kokubo, K., Matsumasa, K., Miura, M., and Nomura, M. J. Org. Chem. 1997, 62, 4564
19. Kokubo, K., Matsumasa, K., Nishinaka, Y., Miura, M., and Nomura, M. Bull. Chem. Soc. Jpn. 1999, 72, 303
20. For pioneering studies on the use of sulfur-containing, chelating hydroacylation substrates, see
21. Bendorf, H. D., Colella, C. M., Dixon, E. C., Marchetti, M., Matukonis, A. N., Musselman, J. D., and Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031
22. Reference 9b.
23. For other uses of chiral mono- and diphosphine spiro ligands in asymmetric catalysis, see
24. Xie, J.-H. and Zhou, Q.-L. Acc. Chem. Res. 2008, 41, 581
25. See the Supporting Information for complete details on ligand screening.
26. Olefin 2a and related substrates were tested in Rh-catalyzed hydroformylation reactions in an attempt to generate branched regioisomers, but regioselectivities were moderate; see
27. Campi, E. M., Jackson, W. R., Perlmutter, P., and Tasdelen, E. E. Aust. J. Chem. 1993, 46, 995
28. In a reaction between 1a and 2a, using the conditions of Table 2, but without any added base, trace conversion to 3aa (∼2%) was observed after 48 h.
29. For a recent application of alkyl aryl sulfides in Ni-catalyzed alkenylative cross-coupling reactions with Grignard reagents, see
30. Ishizuka, K., Seike, H., Hatakeyama, T., and Nakamura, M. J. Am. Chem. Soc. 2010, 132, 13117
31. For a recent report that demonstrates the effects of silver salts in enantioselective intramolecular ketone hydroacylation, see
32. Phan, D. H. T., Kim, B., and Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608
33. Willis has used β-thioacetal-substituted aldehydes as chelating substrates in intermolecular hydroacylation; see
34. Willis, M. C., Randell-Sly, H. E., Woodward, R. L., and Currie, G. S. Org. Lett. 2005, 7, 2249
35. Willis, M. C., Randell-Sly, H. E., Woodward, R. L., McNally, S. J., and Currie, G. S. J. Org. Chem. 2006, 71, 5291
36. Tanaka attempted enantioselective hydroacylation of 1,2-disubstituted and trisubstituted acrylamides, but product racemization and low yields were observed; see ref 6.
37. Both (E)-olefin 5 and (Z)-olefin 6 underwent hydroacylation to give the same enantiomer of 7. See the Supporting Information for further discussion.
38. Initial attempts at intermolecular hydroacylation between salicylaldehyde and olefins bearing other heteroatom-based directing groups were unsuccessful. See the Supporting Information for details.
39. Krafft, M. E., Juliano, C. A., Scott, I. L., Wright, C., and McEachin, M. D. J. Am. Chem. Soc. 1991, 113, 1693
40. Krafft, M. E., Wilson, A. M., Fu, Z., Procter, M. J., and Dasse, O. A. J. Org. Chem. 1998, 63, 1748
41. Perales, J. B. and Van Vranken, D. L. J. Org. Chem. 2001, 66, 7270
42. Substrate chelation is also invoked to explain reactivity in Tanakas enantioselective intermolecular hydroacylation of 1,1-disubstituted acrylamides, which yield β-substituted products; see ref 6.
43. For a detailed study on controlling selectivity for intermolecular alkene or aldehyde hydroacylation using β-S-substituted aldehydes, see
44. Pawley, R. J., Moxham, G. L., Dallanegra, R., Chaplin, A. B., Brayshaw, S. K., Weller, A. S., and Willis, M. C. Organometallics 2010, 29, 1717
45. For examples of substrate-directed olefin functionalizations, see
46. Hoveyda, A. H., Evans, D. A., and Fu, G. C. Chem. Rev. 1993, 93, 1307 In hydroformylation applications, see: Breit, B. Acc. Chem. Res. 2003, 36, 264