Multi-product classes obtained from allylation of α-halo ketones with allylzinc bromide

Chemistry - A European Journal

Volumn 15, Issue 41, 2009, Pages 10732-10735

  Zhang, Min ^a   Hu, Yuanyuan ^a   Zhang, Songlin ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

Allylation; Allylzinc bromide; Epoxides; Ketones; Selectivity

Indexed keywords

ALLYLATION; ALLYLATIONS; ALLYLZINC BROMIDE; EPOXIDES; HOMOALLYLIC ALCOHOL; INDUSTRIAL PRODUCT; MULTI-PRODUCTS; NON-CATALYTIC; ONE-POT SYNTHESIS; PTOLUENESULFONIC ACID; REACTION MECHANISM; SELECTIVITY; YTTERBIUM TRIFLATE;

ALDEHYDES; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL); YTTERBIUM;

KETONES;

EID: 70350233358     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901487     Document Type: Article

References (22)

1. a) C. Gunanathan, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc. 2009, 131, 3146;
2. b) L. C. Campeau, D. J. Schipper, K. Fagnou, J. Am. Chem. Soc. 2008. 130, 3266;
3. c) V. A. Chebanov, V. E. Saraev, S. M. Desenko, V. N. Chernenko, I. V. Knyazeva, U. Groth, T. N. Glasnov, C. O. Kappe, J. Org. Chem. 2008, 73, 5110;
4. d) V. Nair, N. Abhilash, P. B. Beneesh, E. Suresh, Org. Lett. 2005, 7. 4625;
5. e) L. Bagnell, T. Cablewski, C. R. Strauss. R. W. Trainor, J. Org. Chem. 1996, 61. 7355;
6. f) M. Sánchez-Roselló A. L. A. Puchlopek, A. J. Morgan, S. J. Miller, J. Org. Chem. 2008, 73. 1774;
7. g) C. C. Lee, Y. C. Lin, Y. H. Liu, Y. Wang, Organometallics 2005, 24, 136.
8. a) O. A. Wong, Y. Shi, Chem. Rev. 2008. 108, 3958;
9. b) P. Besse, H. Veschambre, Tetrahedron 1994, 50, 8885.
10. a) E. N. Jacobsen, M. H. Wu in Comprehensive Asymmetric Catalysis II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999; Chapter 18, p. 649;
11. b) B. C. Ranu, U Jana, J. Org. Chem. 1998. 63, 8212:
12. c) I. Karamé, M. L. Tommasino. M. Lemaire, Tetrahedron Lett. 2003, 44. 7687-7689:
13. d) M. W. C. Robinson, K. S. Pillinger, A. E. Graham, Tetrahedron Lett. 2006. 47. 5919-5921.
14. J. Meinwald, S. S. Labana, M. S. Chadha, J. Am. Chem. Soc. 1963. 85. 582.
15. P. Knochel. P. Jones. Organozinc Reagents: A Practical Approach. Oxford University Press. New York. 1999.
16. a) L. Stahl, I. P. Smoliakova in Comprehensive Organometallic Chemistry III. Elsevier. Amsterdam. 2007. Chapter 2.06. pp. 309-418:
17. b) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93. 2117.
18. a) M. Kosugi, H. Arai, A. Yoshino. T. Migita. Chem. Lett. 1978, 795:
19. b) I. Pri-Bar, P. S. Pearlman. J. K. Stille, J. Org. Chem. 1983. 48, 4629:
20. c) K. Yano, Y. Hatta, A. Baba, Synthesis 1992. 693-696:
21. d) I. Shibata, S. Fukuoka, A. Baba, Chem. Lett. 1998, 533-534.
22. J. A. Shin, K. II Choi. A. N. Pae, H. Y. Koh, H. Y. Kang, Y. S. Cho, J. Chem. Soc. Perkin Trans. 1 2001, 946-948.