Organic reactions in water: An efficient zinc-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes using unactivated alkyl halides

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3349-3352

  Das, Biswanath ^a   Banerjee, Joydeep ^a   Mahender, Gurram ^a   Majhi, Anjoy ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HALIDE; NITRILE; WATER; ZINC;

AQUEOUS SOLUTION; ARTICLE; ROOM TEMPERATURE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 4644342250     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048721g     Document Type: Article

References (32)

1. (a) Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
2. (b) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811 and references therein.
3. (a) Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
4. (b) Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213.
5. (c) Basavaiah, D.; Bakthadoss, M.; Pandiaraju, S. J. Chem. Soc., Chem. Commun. 1998, 1639.
6. (a) Bradshaw, J. W. S.; Baker, R.; Howse, P. E. Nature 1975, 258, 230.
7. (b) Rossi, R.; Carpita, A.; Messari, T. Synth. Commun. 1992, 22, 603.
8. (c) Garson, M. J. Chem. Rev. 1993, 93, 1699.
9. Marfort, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1979, 44, 3888.
10. (a) Masaki, Y.; Sakuma, K.; Kaji, K. J. Chem. Soc., Chem. Commun. 1980, 434.
11. (b) Brown, H. C.; Basavaiah, D. J. Org. Chem. 1982, 47, 5407.
12. (c) Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386.
13. (d) Navarre, L.; Darses, S.; Genet, J. P. Chem. Commun. 2004, 1108.
14. (d) Amri, H.; Rambaud, M.; Villieras, J. Tetrahedron 1990, 46, 3535.
15. Basavaiah, D.; Sarma, P. K. S.; Bhavani, A. K. D. J. Chem. Soc., Chem. Commun. 1994, 1091.
16. (a) Biswanath, D.; Joydeep, B.; Ravindranath, N.; Venkataiah, B. Tetrahedron Lett. 2004, 45, 2425.
17. (b) Biswanath, D.; Joydeep, B.; Ravindranath, N. Tetrahedron 2004 In press.
18. Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997 and references therein.
19. (a) Li, C. J.; Wei, C.; Keh, C. C. K. J. Am. Chem. Soc. 2003, 125, 4062.
20. (b) Organozinc Reagents: A Practical Approach; Knochel, P., Jones, P., Eds. Oxford University Press: New York, 1999.
21. Synthesis of amino acid derivatives and amines has been reported before utilizing zinc in aqueous medium: Huang, T. S.; Keh, C. C. K.; Li, C. J. Chem. Commun. 2002, 2440. Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131.
22. Synthesis of amino acid derivatives and amines has been reported before utilizing zinc in aqueous medium: Huang, T. S.; Keh, C. C. K.; Li, C. J. Chem. Commun. 2002, 2440. Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131.
23. 4Cl solution (6 mL) was stirred for 10-14 h at room temperature. After the reaction was completed (monitored by TLC), EtOAc (15 mL) was added and shaken. The organic layer was separated and the aqueous layer extracted with EtOAc (3 x 10 mL). The combined organic portion was washed with brine (3 x 10 mL) followed by water (3 x 10 mL), dried, filtered, and concentrated. The residue was subsequently subjected to column chromatography over silica gel to afford pure trisubstituted alkene.
24. 2 = alkyl never produced (Z)-isomer solely. For example, see ref 6.
25. (a) Larson, G. L.; deKaifer, C. F.; Seda, R.; Torres L. E.; Ramirez, J. R. J. Org. Chem. 1984, 49, 3385.
26. (b) Baraldi, P. G.; Guarneri, M.; Pollini, G. P.; Simoni, D.; Barco, A.; Benetti, S. J. Chem. Soc., Perkin Trans. 1 1984, 2501.
27. (c) Boche, G.; Buckl, K.; Martens, D.; Schneider, D. R. Tetrahedron Lett. 1979, 4967.
28. (d) Minami, I.; Yuhara, M.; Shimizu, I.; Tsuji, J. J. Chem. Soc., Chem. Commun. 1986, 118.
29. For similar examples, see: (a) Sorek, Y.; Cohen, H.; Meyerstein, D. J. Chem. Soc., Faraday Trans. 1 1986, 82, 3431. (b) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564.
30. For similar examples, see: (a) Sorek, Y.; Cohen, H.; Meyerstein, D. J. Chem. Soc., Faraday Trans. 1 1986, 82, 3431. (b) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564.
31. Chan, T. H. Pure Appl. Chem. 1996, 52, 5643.
32. Basavaiah, D.; Suguna hyma, R. Tetrahedron 1996, 52, 1253 and references therein.