Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

Chemical Communications

Volumn 48, Issue 83, 2012, Pages 10319-10321

  Cui, Yi ^a   Yamashita, Yasuhiro ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE; ALLYLZINC DERIVATIVE; BORON; BORONIC ACID DERIVATIVE; CARBONYL DERIVATIVE; ELECTROPHILE; HYDRAZONE DERIVATIVE; IMINE; UNCLASSIFIED DRUG; ZINC; ZINC AMIDE;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84866912500     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc34340a     Document Type: Article

References (47)

1. J. Tsuji, Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 2000
2. R. H. Crabtree, The Organometallic Chemistry of the Transition Metals, John Wiley & Sons, Inc., Hoboken, 2005
3. M. B. Smith and M. Jerry, Advanced Organic Chemistry: Reactions, Mechanisms, and Structures, Wiley-Interscience, New York, 2007
4. V. H. Gessner, C. Daschlein, C. Strohmann, Chem. Eur. J., 2009, 15, 3320
5. J. A. Marshall, Chem. Rev., 2000, 100, 3163
6. P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu, Angew. Chem., Int. Ed., 2003, 42, 4302
7. P. Knochel, J. J. Perea, P. Jones, Tetrahedron, 1998, 54, 8275
8. D. E. Frantz, R. Faessler, C. S. Tomooka, E. M. Carreira, Acc. Chem. Res., 2000, 33, 373
9. L. Pu, H.-B. Yu, Chem. Rev., 2001, 101, 757
10. Z. Rappoport and I. Marek, The Chemistry of Organozinc Compounds, John Wiley & Sons, Ltd, Chichester, 2006
11. R. Wada, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2004, 126, 8910
12. S. H. Yu, M. J. Ferguson, R. McDonald, D. G. Hall, J. Am. Chem. Soc., 2005, 127, 12808
13. S. Lou, P. N. Moquist, S. E. Schaus, J. Am. Chem. Soc., 2006, 128, 12660
14. D. S. Barnett, P. N. Moquist, S. E. Schaus, Angew. Chem., Int. Ed., 2009, 48, 8679
15. P. Zhang, J. P. Morken, J. Am. Chem. Soc., 2009, 131, 12550
16. P. Jain, J. C. Antilla, J. Am. Chem. Soc., 2010, 132, 11884
17. S. Kobayashi, H. Ishitani, Chem. Rev., 1999, 99, 1069
18. G. Alvaro, D. Savoia, Synlett, 2002, 651
19. H. Ding, G. K. Friestad, Synthesis, 2005, 2815
20. J. E. Kropf, I. C. Meigh, M. W. P. Bebbington, S. M. Weinreb, J. Org. Chem., 2006, 71, 2046
21. M. Bellaesoued, Y. Frangin, M. Gaudemar, J. Organomet. Chem., 1979, 166, 1
22. B. B. Snider, Acc. Chem. Res., 1980, 13, 426
23. J. M. Chalker, A. Yang, K. Deng, T. Cohen, Org. Lett., 2007, 9, 3825
24. G. Wei, J. M. Chalker, T. Cohen, J. Org. Chem., 2011, 76, 7912
25. C. Patrier, J. Luche, J. Org. Chem., 1985, 50, 910
26. C. Petrier, J. Einhom, J. L. Luche, Tetrahedron Lett., 1985, 26, 1449
27. C. Jubert, P. Knochel, J. Org. Chem., 1992, 57, 5425
28. T. Mejuch, M. Botoshansky, I. Marek, Org. Lett., 2011, 13, 3604
29. P. Knochel, H. Leuser, L.-Z. Gong, S. Perrone and F. F. Kneisel, Handbook of Functionalized Organometallics, Wiley-VCH, Weinheim, 2005
30. M. Fujita, T. Nagano, U. Schneider, T. Hamada, C. Ogawa, S. Kobayashi, J. Am. Chem. Soc., 2008, 130, 2914
31. S. Kobayashi, T. Endo, U. Schneider, M. Ueno, Chem. Commun., 2010, 46, 1260
32. S. Kobayashi, T. Endo, M. Ueno, Angew. Chem., Int. Ed., 2011, 50, 12262
33. K. R. Fandrick, D. R. Fandrick, J. J. Gao, J. T. Reeves, Z. Tan, W. Li, J. J. Song, B. L. Song, N. K. Yee, C. H. Senanayake, Org. Lett., 2010, 12, 3748
34. M. Hatano, K. Ishihara, Synthesis, 2008, 1647
35. S. E. Denmark, S. T. Nguyen, Org. Lett., 2009, 11, 781
36. M. Yus, J. C. Gonzalez-Gomez, F. Foubelo, Chem. Rev., 2011, 111, 7774
37. M. Vasylyev, H. Alper, J. Org. Chem., 2010, 75, 2710
38. Y. Oda, T. Sato, N. Chida, Org. Lett., 2012, 14, 950
39. S.-W. Li, R. A. Batey, Chem. Commun., 2004, 1382
40. B. Dhudshia, J. Tiburcio, A. N. Thadani, Chem. Commun., 2005, 5551
41. R. Wada, T. Shibuguchi, S. Makino, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2006, 128, 7687
42. S. Lou, P. N. Moquist, S. E. Schaus, J. Am. Chem. Soc., 2007, 129, 15398
43. X.-W. Sun, L. Min, M.-H. Xu, G.-Q. Lin, Org. Lett., 2008, 10, 1259
44. U. Schneider, S. Kobayashi, Angew. Chem., Int. Ed., 2007, 46, 5909
45. U. Schneider, M. Ueno, S. Kobayashi, J. Am. Chem. Soc., 2008, 130, 13824
46. T. J. Barker, E. R. Jarvo, Org. Lett., 2009, 11, 1047
47. D. Lee, J. F. Hartwig, Org. Lett., 2005, 7, 1169