Catalyst- and solvent-dependent stereodivergence in the intramolecular Et2Zn/Pd0-promoted carbonyl propargylation: Mechanistic implications

Chemistry - A European Journal

Volumn 19, Issue 41, 2013, Pages 13893-13900

  Arrate, Mõnica ^a   Durana, Aritz ^a   Lorenzo, Paula ^b   De Lera, Ángel R ^b   Álvarez, Rosana ^b   Aurrecoechea, José M ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF VIGO   (Spain)

Author keywords

allenylpalladium; cyclization; palladium; propargylic compounds; stereoselectivity; transmetalation

Indexed keywords

ALLENYLPALLADIUM; CARBONYL PROPARGYLATION; COMPUTATIONAL RESULTS; DIASTEREO-SELECTIVITY; ELECTRON-DONATING ABILITY; INTRAMOLECULAR COUPLING; PROPARGYLIC COMPOUNDS; TRANSMETALATION;

CYCLIZATION; KETONES; LIGANDS; PALLADIUM; PHOSPHORUS COMPOUNDS; SOLVENTS; STEREOSELECTIVITY; ZINC;

ORGANIC SOLVENTS;

DRUG DERIVATIVE; LIGAND; ORGANOMETALLIC COMPOUND; PALLADIUM; PARGYLINE; SOLVENT; ZINC;

ALLENYLPALLADIUM; ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; PROPARGYLIC COMPOUNDS; STEREOCHEMISTRY; STEREOISOMERISM; TRANSMETALATION;

ALLENYLPALLADIUM; CYCLIZATION; PALLADIUM; PROPARGYLIC COMPOUNDS; STEREOSELECTIVITY; TRANSMETALATION;

CATALYSIS; LIGANDS; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PARGYLINE; SOLVENTS; STEREOISOMERISM; ZINC;

EID: 84885389383     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301170     Document Type: Article

References (66)

1. J. A. Marshall, Chem. Rev. 2000, 100, 3163-3185.
2. J. A. Marshall, J. Org. Chem. 2007, 72, 8153-8166.
3. C.-H. Ding, X.-L. Hou, Chem. Rev. 2011, 111, 1914-1937.
4. J. A. Marshall, X. J. Wang, J. Org. Chem. 1991, 56, 6264-6266.
5. Y. Yoshida, T. Nakagawa, F. Sato, Synlett 1996, 437-438.
6. I. Kadota, D. Hatakeyama, K. Seki, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 3059-3062.
7. S. M. Weinreb, D. T. Smith, J. Jin, Synthesis 1998, 509-521.
8. J. M. Aurrecoechea, R. Fañanás, M. Arrate, J. M. Gorgojo, N. Aurrekoetxea, J. Org. Chem. 1999, 64, 1893-1901.
9. J. M. Aurrecoechea, R. Fañanás, B. Lõpez, ARKIVOC 2000, 1, 124-139.
10. J. M. Aurrecoechea, B. Lõpez, M. Arrate, J. Org. Chem. 2000, 65, 6493-6501.
11. J. M. Aurrecoechea, J. H. Gil, B. Lõpez, Tetrahedron 2003, 59, 7111-7121.
12. J. M. Aurrecoechea, M. Arrate, B. Lõpez, Synlett 2001, 872-874.
13. S. Kitagaki, S. Teramoto, Y. Ohta, H. Kobayashi, M. Takabe, C. Mukai, Tetrahedron 2010, 66, 3687-3694.
14. T. Hameury, J. Guillemont, L. Van Hijfte, V. Bellosta, J. Cossy, Org. Lett. 2009, 11, 2397-2400.
15. T. Hirashita, Y. Suzuki, H. Tsuji, Y. Sato, K. Naito, S. Araki, Eur. J. Org. Chem. 2012, 5668-5672.
16. B. W. Gung, X. W. Xue, N. Knatz, J. A. Marshall, Organometallics 2003, 22, 3158-3163.
17. J. A. Marshall, N. D. Adams, J. Org. Chem. 1998, 63, 3812-3813.
18. J. A. Marshall, N. D. Adams, J. Org. Chem. 1999, 64, 5201-5204.
19. Y. Tamaru, S. Goto, A. Tanaka, M. Shimizu, M. Kimura, Angew. Chem. 1996, 108, 962-963
20. Angew. Chem. Int. Ed. Engl. 1996, 35, 878-880.
21. T. Sakamoto, K. Takahashi, T. Yamazaki, T. Kitazume, J. Org. Chem. 1999, 64, 9467-9474.
22. C. Amatore, A. Jutand, J. Organomet. Chem. 1999, 576, 254-278
23. C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321.
24. C. A. Tolman, Chem. Rev. 1977, 77, 313-348.
25. H. Clavier, S. P. Nolan, Chem. Commun. 2010, 46, 841-861.
26. T. Harada, A. Oku, in Organozinc Reagents (Eds.:, P. Knochel, P. Jones,), Oxford University Press, 1999, pp. 101-117.
27. F. Bernaud, E. Vrancken, P. Mangeney, Synlett 2004, 1080-1082.
28. For allenylzinc additions to aromatic aldehydes, the syn/anti ratio has been shown to be dependent on the aromatic ring substituent; see:, F. Ferreira, A. Denichoux, F. Chemla, J. Bejjani, Synlett 2004, 2051-2065.
29. C. J. Elsevier, P. M. Stehouwer, H. Westmijze, P. Vermeer, J. Org. Chem. 1983, 48, 1103-1105.
30. C. J. Elsevier, H. Kleijn, J. Boersma, P. Vermeer, Organometallics 1986, 5, 716-720.
31. J. F. Poisson, F. Chemla, J. F. Normant, Synlett 2001, 305-307.
32. J. Bejjani, C. Botuha, F. Chemla, F. Ferreira, S. Magnus, A. Pérez-Luna, Organometallics 2012, 31, 4876-4885.
33. C. J. Elsevier, P. Vermeer, J. Org. Chem. 1985, 50, 3042-3045.
34. J. A. Marshall, H. R. Chobanian, M. M. Yanik, Org. Lett. 2001, 3, 3369-3372.
35. L. G. Quan, V. Gevorgyan, Y. Yamamoto, J. Am. Chem. Soc. 1999, 121, 3545-3546
36. V. Gevorgyan, L. G. Quan, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 4089-4092
37. X. J. Gai, R. Grigg, S. Collard, J. E. Muir, Chem. Commun. 2000, 1765-1766
38. L. G. Quan, M. Lamrani, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 4827-4828
39. L. Zhao, X. Y. Lu, Angew. Chem. 2002, 114, 4519-4521
40. Angew. Chem. Int. Ed. 2002, 41, 4343-4345
41. O. A. Wallner, K. J. Szabo, Chem. Eur. J. 2003, 9, 4025-4030
42. D. Solé, L. Vallverdu, X. Solans, M. Font-Bardia, J. Bonjoch, J. Am. Chem. Soc. 2003, 125, 1587-1594
43. O. A. Wallner, K. J. Szabo, J. Org. Chem. 2003, 68, 2934-2943
44. A. Flahaut, K. Toutah, P. Mangeney, S. Roland, Eur. J. Inorg. Chem. 2009, 5422-5432
45. H. A. Wang, X. L. Han, X. Y. Lu, Tetrahedron 2010, 66, 9129-9134
46. S.-F. Zhu, X.-C. Qiao, Y.-Z. Zhang, L.-X. Wang, Q.-L. Zhou, Chem. Sci. 2011, 2, 1135-1140
47. D. P. Hruszkewycz, J. Wu, N. Hazari, C. D. Incarvito, J. Am. Chem. Soc. 2011, 133, 3280-3283
48. I. Fernández, D. Solé, M. A. Sierra, J. Org. Chem. 2011, 76, 1592-1598.
49. A. Gillie, J. K. Stille, J. Am. Chem. Soc. 1980, 102, 4933-4941.
50. M. Pérez-Rodríguez, A. A. C. Braga, M. García- Melchor, M. H. Pérez-Temprano, J. A. Casares, G. Ujaque, A. R. de Lera, R. Álvarez, F. Maseras, P. Espinet, J. Am. Chem. Soc. 2009, 131, 3650-3657.
51. R. Álvarez, A. R. de Lera, J. M. Aurrecoechea, A. Durana, Organometallics 2007, 26, 2799-2802.
52. G. A. Chass, C. J. O'Brien, N. Hadei, E. A. B. Kantchev, W. H. Mu, D. C. Fang, A. C. Hopkinson, I. G. Csizmadia, M. G. Organ, Chem. Eur. J. 2009, 15, 4281-4288.
53. Q. Liu, Y. Lan, J. Liu, G. Li, Y. D. Wu, A. W. Lei, J. Am. Chem. Soc. 2009, 131, 10201-10210.
54. D. G. Musaev, L. S. Liebeskind, Organometallics 2009, 28, 4639-4642.
55. B. Fuentes, M. García-Melchor, A. Lledõs, F. Maseras, J. A. Casares, G. Ujaque, P. Espinet, Chem. Eur. J. 2010, 16, 8596-8599.
56. A. B. González-Pérez, R. Álvarez, O. Nieto Faza, Á. R. de Lera, J. M. Aurrecoechea, Organometallics 2012, 31, 2053-2058.
57. A. Ricci, F. Angelucci, M. Bassetti, C. Lo Sterzo, J. Am. Chem. Soc. 2002, 124, 1060-1071.
58. P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808-4839
59. Angew. Chem. Int. Ed. 2004, 43, 4704-4734.
60. K. Yasui, K. Fugami, S. Tanaka, Y. Tamaru, J. Org. Chem. 1995, 60, 1365-1380.
61. J. Terao, N. Kambe, Acc. Chem. Res. 2008, 41, 1545-1554.
62. T. Harada, T. Katsuhira, A. Osada, K. Iwazaki, K. Maejima, A. Oku, J. Am. Chem. Soc. 1996, 118, 11377-11390.
63. Y. Tamaru, J. Organomet. Chem. 1999, 576, 215-231.
64. M. Uchiyama, M. Kameda, O. Mishima, N. Yokoyama, M. Koike, Y. Kondo, T. Sakamoto, J. Am. Chem. Soc. 1998, 120, 4934-4946.
65. W. Clegg, B. Conway, E. Hevia, M. D. McCall, L. Russo, R. E. Mulvey, J. Am. Chem. Soc. 2009, 131, 2375-2384.
66. P. Knochel, M. I. Calaza, E. Hupe, in Metal-Catalyzed Cross-Coupling Reactions Vol. 2, 2 nd ed., (Eds.: A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004, pp. 619-670.