Erratum: Preparation of organoaluminum reagents from propargylic bromides and aluminum activated by PbCl2 and their regio- and diastereoselective addition to carbonyl derivatives (Chemistry - A European Journal (2010) 16 (9829-9834) DOI: 10.1002/chem.201000523);Preparation of organoaluminum reagents from propargylic bromides and aluminum activated by PbCl2and their regio- And diastereoselective addition to carbonyl derivatives

Chemistry - A European Journal

Volumn 16, Issue 32, 2010, Pages 9829-9834

  Guo, Li Na ^a   Gao, Hongjun ^a   Mayer, Peter ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Aluminum; Diastereoselectivity; Lead chloride; Organoaluminum; Propargylic bromide; aluminum; diastereoselectivity; lead chloride; organoaluminum; propargylic bromide

Indexed keywords

ALUMINUM; ALUMINUM CHLORIDE; CARBONYL COMPOUNDS; CHLORINE COMPOUNDS; LEAD COMPOUNDS; STEREOSELECTIVITY;

CARBONYL DERIVATIVES; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE ADDITIONS; HOMOPROPARGYLIC ALCOHOLS; LEAD CHLORIDES; ORGANOALUMINUM; ORGANOALUMINUM REAGENTS; PROPARGYLIC BROMIDE;

ALUMINUM COMPOUNDS;

EID: 77955894421     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201190232     Document Type: Erratum

References (51)

1. B. M. Trost, Science 1991, 254, 1471-1477.
2. R. D. Rieke, M. V. Hanson, Tetrahedron 1997, 53, 1925-1956, and references therein.
3. a) A. Krasovskiy, V. Malakhov, A. Gavryushin, P. Knochel, Angew. Chem. 2006, 118, 6186-6190;
4. Angew. Chem. Int. Ed. 2006, 45, 6040-6044;
5. b) N. Boudet, S. Sase, P. Sinha, C.-Y. Liu, A. Krasovskiy, P. Knochel, J. Am. Chem. Soc. 2007, 129, 12358-12359.
6. a) F. M. Piller, P. Appukkuttan, A. Gavryushin, M. Helm, P. Knochel, Angew. Chem. 2008, 120, 6907-6911;
7. Angew. Chem. Int. Ed. 2008, 47, 6802-6806;
8. b) A. Metzger, F. M. Piller, P. Knochel, Chem. Commun. 2008, 5824-5826.
9. a) Y.-H. Chen, P. Knochel, Angew. Chem. 2008, 120, 7760-7763;
10. Angew. Chem. Int. Ed. 2008, 47, 7648-7651;
11. b) Y.-H. Chen, M. Sun, P. Knochel, Angew. Chem. 2009, 121, 2270-2273;
12. Angew. Chem. Int. Ed. 2009, 48, 2236-2239.
13. K. Takai, T. Ueda, T. Hayashi, T. Moriwake, Tetrahedron Lett. 1996, 37, 7049-7052.
14. T. Blümke, Y.-H. Chen, Z. Peng, P. Knochel, Nat. Chem. Biol. 2010, 2, 313-318.
15. 2/3Br.
16. a) R. G. Daniels, L. A. Paquette, Tetrahedron Lett. 1981, 22, 1579-1582;
17. b) M. J. Lin, T. P. Loh, J. Am. Chem. Soc. 2003, 125, 13042-13043;
18. c) W. Miao, L.W. Chung, Y.-D. Wu, T. H. Chan, J. Am. Chem. Soc. 2004, 126, 13326-13334.
19. a) M. Gaudemar, Ann. Chim. (Cachan Fr.) 1956, 1, 161-213;
20. b) M. Gaudemar, Bull. Soc. Chim. Fr. 1958, 1475-1477.
21. K. Eiter, H. Oediger, Justus Liebigs Ann. 1965, 682, 62-70.
22. a) F. Sondheimer, Y. Amiel, Y. Gaoni, J. Am. Chem. Soc. 1962, 84, 270-274;
23. b) E. Crundwell, A. L. Cripps, J. Med. Chem. 1972, 15, 754-756;
24. c) G. Picotin, P. Miginiac, J. Org. Chem. 1985, 50, 1299-1301;
25. d) L. Leboutet, G. C. L. Miginiac, J. Organomet. Chem. 1991, 420, 155-161.
26. For general activation of Al powder, see: S. Saito, Science of Synthesis (Houben-Weyl), Vol. 7 (Ed.: H. Yamamoto), 2004, pp. 5-14.
27. 2 for insertion to allyl bromide and chloride, see: a) K. Uneyama, N. Kamaki, A. Moriya, S. Torii, J. Org. Chem. 1985, 50, 5396-5399;
28. b) H. Tanaka, S. Yamashita, T. Hamatani, Y. Ikemoto, S. Torii, Synth. Commun. 1987, 17, 789-794;
29. c) M. Wada, H. Ohki, K.-y. Akiba, Bull. Chem. Soc. Jpn. 1990, 63, 1738-1747;
30. d) S. Araki, S.-J. Jin, Y. Idou, Y. Butsugan, Bull. Chem. Soc. Jpn. 1992, 65, 1736-1738;
31. e) R. H. Khan, T. S. R. Prasada Rao, J. Chem. Res. Synop. 1998, 202-203.
32. For selected examples, see: a) H. Yamamoto in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991;
33. b) S. Kobayashi, K. Nishio, J. Am. Chem. Soc. 1995, 117, 6392-6393;
34. c) M. B. Isaac, T.-H. Chan, J. Chem. Soc. Chem. Commun. 1995, 1003-1004;
35. d) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472-7480;
36. e) Z. Li, Y. Jia, J. Zhou, Synth. Commun. 2000, 30, 2515-2524;
37. f) T. P. Loh, M. J. Lin, K. L. Tan, Tetrahedron Lett. 2003, 44, 507-509;
38. g) A. S.-Y. Lee, S.-F. Chu, Y.-T. Chang, S.-H. Wang, Tetrahedron Lett. 2004, 45, 1551-1553;
39. h) P. H. Lee, H. Kim, K. Lee, Adv. Synth. Catal. 2005, 347, 1219-1222;
40. i) J. M. Huang, H. C. Luo, Z. X. Chen, G. C. Yang, T. P. Loh, Eur. J. Org. Chem. 2008, 295-298;
41. j) X. Ma, J.-X. Wang, S. Li, K.-H. Wang, D. Huang, Tetrahedron 2009, 65, 8683-8689.
42. J. A. Marshall, N. D. Adams, J. Org. Chem. 1998, 63, 3812-3813.
43. a) T. Takeda, M. Ando, T. Sugita, A. Tsubouchi, Org. Lett. 2007, 9, 2875-2878;
44. b) J. Tummatorn, G. B. Dudley, J. Am. Chem. Soc. 2008, 130, 5050-5051.
45. Y.-B. Zhao, Z.-Y. Yan, Y.-M. Liang, Tetrahedron Lett. 2006, 47, 1545-1549.
46. a) Y. Matsumoto, M. Naito, Y. Uozumi, T. Hayashi, J. Chem. Soc. Chem. Commun. 1993, 1468-1469;
47. b) D. Seebach, J. Golinski, Helv. Chim. Acta 1981, 64, 1413-1423.
48. E. Vedejs, O. Daugulis, J. Org. Chem. 1996, 61, 5702-5703.
49. The relative stereochemistry of 4 ik was also determined by its corresponding ester (see the Supporting Information).
50. a) G. Zweifel, G. Hahn, J. Org. Chem. 1984, 49, 4565 - 4567;
51. b) Y. Matsumoto, J. Org. Chem. 1986, 51, 886-891.