Copper-catalyzed enantioselective additions to oxocarbenium ions: Alkynylation of isochroman acetals

Journal of the American Chemical Society

Volumn 133, Issue 43, 2011, Pages 17142-17145

  Maity, Prantik ^a   Srinivas, Harathi D ^a   Watson, Mary P ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLIDES; ALKYNYLATIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE ADDITION; GOOD YIELD; IN-SITU; OXAZOLINES; OXOCARBENIUM; SIMULTANEOUS FORMATION; TERMINAL ALKYNE;

ACETYLENE; CATALYSIS; ENANTIOSELECTIVITY; IONS;

COPPER;

ACETAL; ALKYNE; CARBENOID; COPPER; COPPER ACETYLIDE; ISOCHROMAN DERIVATIVE; LIGAND; OXOCARBENIUM; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; RACEMIC MIXTURE; REACTION ANALYSIS; REACTION OPTIMIZATION; REDUCTION; STEREOCHEMISTRY;

ACETALS; ALKYNES; CHROMANS; COPPER; IONS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 80055022202     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja207585p     Document Type: Article

References (57)

1. Albrecht, U.; Lalk, M.; Langer, P. Bioorg. Med. Chem. 2005, 13, 1531
2. TenBrink, R. E.; Bergh, C. L.; Duncan, J. N.; Harris, D. W.; Huff, R. M.; Lahti, R. A.; Lawson, C. F.; Lutzke, B. S.; Martin, I. J.; Rees, S. A.; Schlachter, S. K.; Sih, J. C.; Smith, M. W. J. Med. Chem. 1996, 39, 2435
3. Xu, J.; Kjer, J.; Sendker, J.; Wray, V.; Guan, H.; Edrada, R.; Muller, W. E. G.; Bayer, M.; Lin, W.; Wu, J.; Proksch, P. Bioorg. Med. Chem. 2009, 17, 7362
4. For an alternative strategy employing conjugate addition, see: Hoveyda, A.; Hird, A.; Kacprzynski, M. Chem. Commun. 2004, 1779
5. Correia, C. A.; Li, C.-J. Heterocycles 2010, 82, 555
6. Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242
7. Hayashi, M.; Inubushi, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 4037
8. Mitchell, T. A.; Bode, J. W. J. Am. Chem. Soc. 2009, 131, 18057
9. Vieira, A. S.; Fiorante, P. F.; Hough, T. L. S.; Ferreira, F. P.; Ludtke, D. S.; Stefani, H. A. Org. Lett. 2008, 10, 5215
10. Vo, C.-V. T.; Mitchell, T. A.; Bode, J. W. J. Am. Chem. Soc. 2011, 133, 14082
11. For enantioselective additions to acyclic oxocarbenium ions (or acetals), see: Evans, D. A.; Thomson, R. J. J. Am. Chem. Soc. 2005, 127, 10506.
12. Kobayashi, S.; Arai, K.; Yamakawa, T.; Chen, Y.-J.; Salter, M. M.; Yamashita, Y. Adv. Synth. Catal. 2011, 353, 1927
13. Coric, I.; Vellalath, S.; List, B. J. Am. Chem. Soc. 2010, 132, 8536
14. Umebayashi, N.; Hamashima, Y.; Hashizume, D.; Sodeoka, M. Angew. Chem., Int. Ed. 2008, 47, 4196
15. Terada, M.; Tanaka, H.; Sorimachi, K. J. Am. Chem. Soc. 2009, 131, 3430
16. Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198
17. Moquist, P. N.; Kodama, T.; Schaus, S. E. Angew. Chem., Int. Ed. 2010, 49, 7096
18. Braun, M.; Kotter, W. Angew. Chem., Int. Ed. 2004, 43, 514
19. Cozzi, Pier G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2004, 2004, 4095
20. Pu, L. Tetrahedron 2003, 59, 9873
21. Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806
22. Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687
23. Boyall, D.; Frantz, D. E.; Carreira, E. M. Org. Lett. 2002, 4, 2605
24. Takita, R.; Yakura, K.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13760
25. Asano, Y.; Hara, K.; Ito, H.; Sawamura, M. Org. Lett. 2007, 9, 3901
26. Koyuncu, H.; Dogan, Ö. Org. Lett. 2007, 9, 3477
27. Yang, F.; Xi, P.; Yang, L.; Lan, J.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 5457
28. Asano, Y.; Ito, H.; Hara, K.; Sawamura, M. Organometallics 2008, 27, 5984
29. Ito, J.-I.; Asai, R.; Nishiyama, H. Org. Lett. 2010, 12, 3860
30. Trost, B. M.; Chan, V. S.; Yamamoto, D. J. Am. Chem. Soc. 2010, 132, 5186
31. Chen, C.; Hong, L.; Xu, Z.-Q.; Liu, L.; Wang, R. Org. Lett. 2006, 8, 2277
32. Zhou, S.; Chen, C.-R.; Gau, H.-M. Org. Lett. 2010, 12, 48
33. Reynolds, T.; Bharadwaj, A.; Scheidt, K. J. Am. Chem. Soc. 2006, 128, 15382
34. Unger, R.; Weisser, F.; Chinkov, N.; Stanger, A.; Cohen, T.; Marek, I. Org. Lett. 2009, 11, 1853
35. Li, F.-Q.; Zhong, S.; Lu, G.; Chan, A. Adv. Synth. Catal. 2009, 351, 1955
36. Mukaiyama, T.; Suzuki, K. Chem. Lett. 1980, 255
37. Huffman, M.; Yasuda, N.; DeCamp, A.; Grabowski, E. J. Org. Chem. 1995, 60, 1590
38. Thompson, A.; Corley, E.; Huntington, M.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 8937
39. Tan, L.; Chen, C.-Y.; Tillyer, R.; Grabowski, E.; Reider, P. Angew. Chem., Int. Ed. 1999, 38, 711
40. Cozzi, P. Angew. Chem., Int. Ed. 2003, 42, 2895
41. Lu, G.; Li, X.; Jia, X.; Chan, W.; Chan, A. Angew. Chem., Int. Ed. 2003, 42, 5057
42. Corey, E.; Cimprich, K. J. Am. Chem. Soc. 1994, 116, 3151
43. Usanov, D. L.; Yamamoto, H. J. Am. Chem. Soc. 2011, 133, 1286
44. Liu, L; Wang, R.; Kang, Y.-F.; Cai, H.-Q.; Chen, C. Synlett 2006, 1245
45. Downey, C.; Johnson, M.; Tracy, K. J. Org. Chem. 2008, 73, 3299
46. Downey, C.; Mahoney, B.; Lipari, V. J. Org. Chem. 2009, 74, 2904
47. DeNinno, M.; Perner, R.; Morton, H.; DiDomenico, S. J. Org. Chem. 1992, 57, 7115
48. Xu, Y.-C.; Lebeau, E.; Gillard, J.; Attardo, G. Tetrahedron Lett. 1993, 34, 3841
49. 6 can be stored outside a glovebox. It has been reported to oxidize in air. See: Kubas, G. J. Inorg. Synth. 1990, 28, 68
50. Das, A.; Chaudhuri, R.; Liu, R.-S. Chem. Commun. 2009, 4046
51. Asano, Y.; Ito, H.; Hara, K.; Sawamura, M. Organometallics 2008, 27, 5984
52. Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763
53. Shi, W.; Luo, Y.; Luo, X.; Chao, L.; Zhang, H.; Wang, J.; Lei, A. J. Am. Chem. Soc. 2008, 130, 14713
54. Wang, X.-S.; Zhao, H.; Li, Y.-H.; Xiong, R.-G.; You, X.-Z. Top. Catal. 2005, 35, 43
55. Badiei, Y. M.; Warren, T. H.; Chiang, K. P.; Holland, P. L. Inorg. Synth. 2010, 35, 50
56. Pérez-Galán, P.; Delpont, N.; Herrero-Gómez, E.; Maseras, F.; Echavarren, A. M. Chem.-Eur. J. 2010, 16, 5324
57. For an example of 1-naphthyl giving significant improvement over phenyl in a reaction that likely involves cation-π interactions, see: Birrell, J. A.; Desrosiers, J.-N.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 13872