Zinc catalyzed and mediated propargylations with propargyl boronates

Organic Letters

Volumn 12, Issue 1, 2010, Pages 88-91

  Fandrick, Daniel R ^a   Fandrick, Keith R ^a   Reeves, Jonathan T ^a   Tan, Zhulin ^a   Johnson, Courtney S ^a   Lee, Heewon ^a   Song, Jinhua J ^a   Yee, Nathan K ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORINIC ACID DERIVATIVE; DRUG DERIVATIVE; KETONE; PARGYLINE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY;

ALDEHYDES; BORINIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MOLECULAR STRUCTURE; PARGYLINE; ZINC;

EID: 73949133468     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902457m     Document Type: Article

References (48)

1. For general reviews of organozinc chemistry, see: Knochel P.; Leuser, H.; Gong, L.-Z.; Perrone, S.; Kneisel, F. F. Handbook of Functionalized Organometallics; Knochel, P., Ed.; Whiley-VCH: Weinheim, 2005; pp 251-346.
2. For examples, see: (a) Marshall, J. A.; Adams, N. D. Org. Lett. 2000, 2, 2897-2900.
3. (b) Marshall, J. A.; Yanik, M. M. J. Org. Chem. 2001, 66, 1373-1379.
4. (c) Marino, J. P.; McClure, M. S.; Holub, D. P.; Comasseto, J. V.; Tucci, F. C. J. Am. Chem. Soc. 2002, 124, 1664-1668.
5. (d) Bahadoor, A. B.; Flyer, A.; Micalizio, G. C. J. Am. Chem. Soc. 2005, 127, 3694-3695.
6. (e) Marshall, J. A. J. Org. Chem. 2007, 72, 8153-8166.
7. (a) Poisson, J.-F.; Normant, J. F. Org. Lett. 2001, 3, 1889-1891.
8. (b) Chemla, F.; Ferreira, F.; Gaucher, X.; Palais, L. Synthesis 2007, 1235-1241.
9. Hameury, T.; Guillemont, J.; Hijfte, L. V.; Bellosta, V.; Cossy, J. Org. Lett. 2009, 11, 2397-2400.
10. (a) Tamaru, Y.; Goto, S.; Tanaka, A.; Shimizu, M.; Kimura, Angew. Chem., Int. Engl. Ed. 1996, 35, 878-880.
11. (b) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812-3813.
12. (c) Marshall, J. A.; Mullhearn, J. J. J. Org. Chem. 2006, 71, 4840-4844.
13. (a) Zakharkin, L. I.; Okhlobystin, O. Y. Z. Obshch. Khim. 1960, 30, 2134-2138.
14. (b) Thiele, K.-H.; Zdunneck, P. J. Organomet. Chem. 1965, 4, 10-17.
15. (c) Thiele, K.-H.; Engelhardt, G.; Kohler, J.; Arnstedt, M. J. Organomet. Chem. 1967, 9, 385-393.
16. For reviews, see: (a) Pu, L. Tetrahedron 2003, 59, 9873-9886.
17. (b) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824.
18. (c) Tejedor, D.; LopezTosco, S.; Cruz-Acosta, F.; Mendez-Abt, G.; Garcia-Tellado, F. Angew. Chem., Int. Engl. Ed. 2009, 48, 2090-2098.
19. For additional examples, see: (d) Jimeno, C.; Sayalero, S.; Fjermestad, T.; Colat, G.; Maseras, F.; Pericas, M. A. Angew. Chem., Int. Engl. Ed. 2008, 47, 1098-1101.
20. (e) Fujita, M.; Nagano, T.; Schneider, U.; Hamada, T.; Ogawa, C.; Kobayashi, S. J. Am. Chem. Soc. 2008, 130, 2914-2915.
21. For selected examples of propargylations and allenylations with boron reagents, see: (a) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131.
22. (b) Ikeda, N.; Arai, I.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 483-486.
23. (c) Corey, E. J.; Yu, C-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878-879.
24. (d) Hernandez, E.; Burgos, C. H.; Alicea, E.; Soderquist, J. A. Org. Lett. 2006, 8, 4089-4091.
25. (a) Schneider, U.; Kobayashi, S. Angew. Chem., Int. Ed. Engl. 2007, 46, 5909-5912.
26. (b) Schneider, U.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2008, 130, 13824-13825.
27. (a) Rauniyar, V.; Zhai, H.; Hall, D. G. J. Am. Chem. Soc. 2008, 130, 8481-8490.
28. (b) Rauniyar, V.; Hall, D. G. J. Org. Chem. 2009, 74, 4236-4241.
29. For selected examples of regioselective TMS-propyne additions to carbonyl species, see: (a) Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 9, 5041-5043.
30. (b) Han, Y.; Huang, Y.-Z. Tetrahedron Lett. 1994, 35, 9433-9434.
31. (c) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2001, 3, 3369-3372.
32. (d) Lin, M.-J.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 13042-13043.
33. (e) Masuyama, Y.; Yamazuki, R.; Ohtsuka, M.; Kurusu, Y. Synlett 2006, 1750-1752.
34. (f) Vrancken, E.; Alouane, N.; Gerard, H.; Mangeney, P. J. Org. Chem. 2007, 72, 1770-1779.
35. Hoffmann, R. W.; Brinkmann, H.; Frenking, G. Chem. Ber. 1990, 123, 2387-2394.
36. Brown, H. C.; Prasad, J. V. N. V. J. Org. Chem. 1986, 51, 4526-4530, and references therein.
37. (a) Mancilla, T.; Carrillo, L.; De La Paz Reducindo, M. Polyhedron 1996, 15, 3777-3785, and references therein.
38. (b) Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, 6716-6717.
39. (c) Lee, S. J.; Gray, K. C.; Paek, J. S.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 466-468.
40. (d) Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 14084-14085.
41. For examples of zinc mediated propargylation to β-ketoamides, see: Taniguchi, M.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1995, 68, 645-653.
42. Organozinc Reagents: A Practical Approach; Knochel, P., Joned, P., Eds.; Oxford Univ. Press.: Oxford, 1999.
43. For examples, see: (a) Wang, K. K.; Liu, C. J. Org. Chem. 1985, 50, 2578-2580.
44. (b) Ikeda, N.; Arai, I.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 483-486.
45. (c) Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1989, 111, 1236-1240.
46. (d) Hernandez, E.; Burgos, C. H.; Alicea, E.; Soderquist, J. A. Org. Lett. 2006, 8, 4089-4091.
47. (e) Paton, R. S.; Goodman, J. M.; Pellegrinet, S. C. Org. Lett. 2009, 11, 37-40.
48. See Supporting Information.