DTBB-catalysed lithiation of 3-functionalised 1-chloropropenes

Tetrahedron

Volumn 54, Issue 22, 1998, Pages 6177-6184

  Gómez, Cecilia ^a   Huerta, Fernando F ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; LITHIUM;

ARTICLE; CATALYSIS; HYDROLYSIS; MOLECULAR DYNAMICS; MOLECULAR STABILITY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032575234     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00310-X     Document Type: Article

References (29)

1. 1. For reviews, see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
2. (b) Nájera, C.; Yus, M. Recent Res. Devel. Org. Chem. 1997, 1, 67-96.
3. 2. For some leading references on intermediates of type I/II from our laboratory, see: (a) Barluenga, J.; Fernández, J. R.; Yus, M. J. Chem. Research (S) 1986, 273; (M) 1986, 2401-2415.
4. 2. For some leading references on intermediates of type I/II from our laboratory, see: (a) Barluenga, J.; Fernández, J. R.; Yus, M. J. Chem. Research (S) 1986, 273; (M) 1986, 2401-2415.
5. (b) Barluenga, J.; Foubelo, F.; Fañanás, F. J.; Yus, M. J. Chem. Research (S) 1989, 200-201; (M) 1989, 1524-1552.
6. (b) Barluenga, J.; Foubelo, F.; Fañanás, F. J.; Yus, M. J. Chem. Research (S) 1989, 200-201; (M) 1989, 1524-1552.
7. (c) Barluenga, J.; Foubelo, F.; González, R.; Fañanás, F. J.; Yus, M. J. Chem. Soc., Chem. Commun. 1990, 587-588.
8. (d) Barluenga, J.; Foubelo, F.; González, R.; Fañanás, F. J.; Yus, M. J. Chem. Soc., Chem. Commun. 1990, 1521-1523.
9. (e) Barluenga, J.; Foubelo, F.; González, R.; Fañanás, F. J.; Yus, M. J. Chem. Soc., Chem. Commun. 1991, 1001-1002.
10. (f) Barluenga, J.; González, R.; Fañanás, F. J.; Yus, M.; Foubelo, F. J. Chem. Soc., Perkin Trans. 1 1994, 1069-1077.
11. 3. Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356-363.
12. 4. (a) For the first account on this reaction, see: Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400.
13. (b) For a recent review, see: Yus, M. Chem. Soc. Rev. 1996, 155-161.
14. 5. Last paper on this topic from our laboratory: Alonso, E.; Ramón, D. J.; Yus, M. Tetrahedron Lett. 1997, 38, 8903-8906.
15. 6. Last paper on this topic from our laboratory: Foubelo, F.; Gutierrez, A.; Yus, M. Tetrahedron Lett. 1997, 38, 4837-4840.
16. 7. (a) Last paper on this topic from our laboratory: Bachki, A.; Falvello, L. R.; Foubelo, F.; Yus, M. Tetrahedron:Asymmetry 1997, 8, 2633-2643.
17. 8. Last paper on this topic from our laboratory: Gómez, C.; Huerta, F. F.; Yus, M. Tetrahedron 1998, 54, 1853-1866.
18. 9. The (Z)-diastereoisomer probably decomposes under the column chromatography conditions employed.
19. 10. (a) For a monograph, see: Blomberg, C. The Barbier Reaction and Related One-step Processes; Springer-Verlag: Berlin, 1993.
20. (b) Alonso, F.; Yus, M. Recent Res. Devel. Org. Chem., in press.
21. 11. Guijarro, A.; Yus, M. Tetrahedron 1994, 50, 13269-13276.
22. 12. This transformation is a well-known reaction usually carried out with phenyl thioethers. (a) For a review, see: Cohen, T.; Buhpathy, M. Acc. Chem. Res. 1989, 22, 152-161.
23. (b) See also reference 5.
24. 13. Choudhury, P. K.; Almena, J.; Foubelo, F.; Yus, M. Tetrahedron 1997, 53, 17373-17382.
25. 14. Butler, G.B.; Ingley, F. L. J. Am. Chem. Soc. 1951, 73, 895-896.
26. 2CH), 6.16 (1H, def dt, J = 14.0, 1.2, CHCl).
27. 16. Engman, L. J. Org. Chem. 1987, 52, 4086-4094.
28. 17. In the case of nitrogen-containing products, the reaction mixture was hydrolysed with 1 M hydrochloric acid (3 × 10 ml) and the aqueous layer was then acidified with 4 M sodium hydroxide before the extraction with ethyl acetate.
29. 18. For this compound was not possible to obtain the corresponding HRMS (EI) due to the low intensity or the absence of the M+ signal.