Copper-catalyzed γ-selective and stereospecific allylic alkylation of ketene silyl acetals

Journal of the American Chemical Society

Volumn 133, Issue 15, 2011, Pages 5672-5675

  Li, Dong ^a   Ohmiya, Hirohisa ^a   Sawamura, Masaya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALKYLATION; ALLYLIC PHOSPHATES; ANTI-SELECTIVITY; CHIRALITY TRANSFER; KETENE SILYL ACETAL; STEREOSPECIFIC; UNSATURATED ESTERS;

CATALYSIS; ESTERS; FUNCTIONAL GROUPS; STEREOCHEMISTRY;

ALKYLATION;

ACETAL DERIVATIVE; ACETIC ACID ETHYL ESTER; ALLYLIC PHOSPHATE; COPPER; KETENE SILYL ACETAL; PHOSPHATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 79954484693     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja111645q     Document Type: Article

References (57)

1. Reviews on transition-metal-catalyzed allylic substitutions: Tsuji, J. Acc. Chem. Res. 1969, 2, 144-152
2. Trost, B. M. Tetrahedron 1977, 33, 2615-2649
3. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422
4. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943
5. Lu, Z.; Ma, S. Angew. Chem. Int. Ed. 2008, 47, 258-297
6. Selected examples of transition-metal-catalyzed enantioselective allylic alkylations with ketone enolates: Trost, B. M.; Shroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759-6760
7. Braun, M.; Laicher, F.; Meier, T. Angew. Chem. Int. Ed. 2000, 39, 3494-3498
8. Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113-4115
9. Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 126, 15044-15045
10. Yan, X.-X.; Liang, C.-G.; Zhang, Y.; Hong, W.; Cao, B.-X.; Dai, L.-X.; Hou, X.-L. Angew. Chem. Int. Ed. 2005, 44, 6544-6546
11. Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 17180-17181
12. Zheng, W.-H.; Zheng, B.-H.; Zhang, Y.; Hou, X.-L. J. Am. Chem. Soc. 2007, 129, 7718-7719
13. Chen, J.-P.; Ding, C.-H.; Liu, W.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2010, 132, 15493-15495
14. Braun, M.; Meier, T. Angew. Chem. Int. Ed. 2006, 45, 6952-6955 and references therein
15. Graening, T.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 127, 17192-17193
16. The regioselectivity in Pd-catalyzed allylic substitutions that involve a (π-allyl)palladium intermediate is highly dependent on the substitution pattern of allylic substrates. See refs 1 and 2a-2i.
17. Rh-catalyzed α-selective allylic alkylations of copper enolates derived from aryl ketones with chiral secondary allylic alcohol derivatives bearing a terminal alkene moiety: Evans, P. A.; Leahy, D. K. J. Am. Chem. Soc. 2003, 125, 8974-8975
18. Evans, P. A.; Lawler, M. J. J. Am. Chem. Soc. 2004, 126, 8642-8643
19. Rh-catalyzed allylic substitution of allylic carbonates having allylic system in the internal position with enoxysilanes occurred competitively at the α- and γ-positions: Muraoka, T.; Matsuda, I.; Itoh, K. Tetrahedron. Lett. 2000, 41, 8807-8811
20. Rh-catalyzed α-selective allylic alkylations of malonates with secondary allylic substrates: Evans, P. A.; Nelson, J. D. Tetrahedron. Lett. 1998, 39, 1725-1728
21. Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581-5582
22. Ashfeld, B. L.; Miller, K. A.; Martin, S. F. Org. Lett. 2004, 6, 1321-1324
23. Ir-catalyzed α-selective allylic alkylations of malonates with secondary allylic substrates: Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647-8655
24. Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742
25. Fe-catalyzed α-selective allylic alkylations of soft carbon nucleophiles with secondary allylic substrates: Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett 1991, 513-514
26. Plietker, B. Angew. Chem. Int. Ed. 2006, 45, 1469-1473
27. Holzwarth, M.; Dieskau, A.; Tabassam, M.; Plietker, B. Angew. Chem. Int. Ed. 2009, 48, 7251-7255
28. Ru-catalyzed α-selective allylic alkylations of malonates with secondary allylic substrates: Trost, B. M.; Fraisse, P. L.; Ball, Z. T. Angew. Chem. Int. Ed. 2002, 41, 1059-1061
29. Kawatsura, M.; Ata, F.; Hayase, S.; Itoh, T. Chem. Commun. 2007, 4283-4285
30. Pd-catalyzed γ-selective and stereospecific allyl-aryl coupling between allylic esters and arylboronic acids: Ohmiya, H.; Makida, Y.; Tanaka, T.; Sawamura, M. J. Am. Chem. Soc. 2008, 130, 17276-17277
31. Ohmiya, H.; Makida, Y.; Li, D.; Tanabe, M.; Sawamura, M. J. Am. Chem. Soc. 2010, 132, 879-889
32. Li, D.; Tanaka, T.; Ohmiya, H.; Sawamura, M. Org. Lett. 2010, 12, 2438-2440
33. Makida, Y.; Ohmiya, H.; Sawamura, M. Chem. Asian J. 2011, 6, 410-414
34. Cu-catalyzed γ-selective and stereospecific allyl-alkyl and allyl-aryl couplings with organoboron compounds: Ohmiya, H.; Yokobori, U.; Makida, Y.; Sawamura, M. J. Am. Chem. Soc. 2010, 132, 2895-2897
35. Ohmiya, H.; Yokokawa, N.; Sawamura, M. Org. Lett. 2010, 12, 2438-2440 Cu-catalyzed conjugate additions of alkylboron compounds (alkyl-9-BBN) to imidazol-2-yl α,β-unsaturated ketones: Ohmiya, H.; Yoshida, M.; Sawamura, M. Org. Lett. 2011, 13, 482-485 Cu-catalyzed carboxylations of alkylboron compounds (alkyl-9-BBN) with carbon dioxide: Ohmiya, H.; Tanabe, M.; Sawamura, M. Org. Lett. 2011, 13, 1086-1088
36. Reviews on Cu-catalyzed allylic substitutions: Hoveyda, A. H.; Hird, A. W.; Kacprzynski, M. A. Chem. Commun. 2004, 1779-1785
37. Yorimitsu, H.; Oshima, K. Angew. Chem. Int. Ed. 2005, 44, 4435-4439
38. Falciola, C. A.; Alexakis, A. Eur. J. Org. Chem. 2008, 3765-3780
39. Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pàmies, O.; Diéguez, M. Chem. Rev. 2008, 108, 2796-2823
40. Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824-2852
41. Transmetalation between Cu(I) complexes and ketene silyl acetals in the Cu(I)-catalyzed carbonyl 1,2-additions of ketene silyl acetals: Oisaki, K.; Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5644-5645
42. Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7164-7165
43. Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 500-501
44. Cu(II)-catalyzed enantioselective Michael additions of enolsilanes: Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407-1415
45. Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325-335
46. Reviews on the Claisen rearrangement: Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452
47. Castro, A. M. M. Chem. Rev. 2004, 104, 2939-3002
48. Rh-catalyzed reductive Claisen rearrangement and discussions about the functional group compatibility of the Ireland-Claisen rearrangement: Miller, S. P.; Morken, J. P. Org. Lett. 2002, 4, 2743-2745
49. Discussions about the functional group compatibility of the Johnson-Claisen rearrangement: Cosgrove, K. L.; McGeary, R. P. Synlett 2009, 1749-1752
50. Cosgrove, K. L.; McGeary, R. P. Tetrahedron 2010, 66, 3050-3057
51. Menéndez Pérez, B.; Hartung, J. Tetrahedron. Lett. 2009, 50, 960-962
52. Unsymmetrically substituted secondary allylic bromides and chlorides are not suitable as substrate because halogenation of the corresponding allylic alcohols is not regioselective. While almost no reaction occurred with a primary allylic bromide, a primary allylic chloride underwent the reaction in a poor product yield with a moderate α-selectivity.
53. Reaction of 1a with methyl isobutyrate-derived ketene silyl acetal resulted in low conversion (35%) and poor yield (13%). The use of propionate-derived bis-trimethylsilyl ketene acetal resulted in no reaction.
54. 1,3-strain. See also refs 11a,11b.
55. The stereochemistry of the α-isomer has not been analyzed.
56. Yoshikai, N.; Zhang, S.-L.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 12862-12863
57. Yamanaka, M.; Kato, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 6287-6293