Pure and Applied Chemistry, 2009, Volume 81, No. 2, pp. 235-246, References

Pure Appl. Chem., 2009, Vol. 81, No. 2, pp. 235-246

http://dx.doi.org/10.1351/PAC-CON-08-08-04

1-Lithio-1,3-dienes as useful building blocks in organic synthesis

Wen-Xiong Zhang and Zhenfeng Xi

Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China

References

1. (a). B. J. Wakefield. The Chemistry of Organolithium Compounds, pp. 116-121, Pergamon, Oxford (1974);
1. (b). J. Clayden. Organolithiums: Selectivity for Synthesis, Pergamon, Oxford (2002);
1. (c). Z. Rappoport, I. Marke (Eds.). The Chemistry of Organolithium Compounds, John Wiley, Chichester (2004).
2. (a). Z. Xi. Eur. J. Org. Chem. 2773 (2004); (http://dx.doi.org/10.1002/ejoc.200400033)
2. (b). J. A. Varela, C. Saa. Chem. Rev. 103, 3787 (2003). (http://dx.doi.org/10.1021/cr030677f)
3. (a). C. Wang, Q. Luo, H. Sun, X. Guo, Z. Xi. J. Am. Chem. Soc. 129, 3094 (2007); (http://dx.doi.org/10.1021/ja070404s)
3. (b). C. Wang, J. Yuan, G. Li, Z. Wang, S. Zhang, Z. Xi. J. Am. Chem. Soc. 128, 4564 (2006); (http://dx.doi.org/10.1021/ja0579208)
3. (c). H. Fang, G. Li, G. Mao, Z. Xi. Chem.Eur. J. 10, 3444 (2004); (http://dx.doi.org/10.1002/chem.200400025)
3. (d). C. Wang, Q. Song, Z. Xi. Tetrahedron 60, 5207 (2004); (http://dx.doi.org/10.1016/S0040-4020(04)00606-4)
3. (e). G. Li, H. Fang, S. Zhang, Z. Xi. Tetrahedron Lett. 45, 8399 (2004); (http://dx.doi.org/10.1016/j.tetlet.2004.09.089)
3. (f). G. Li, H. Fang, Z. Xi. Tetrahedron Lett. 44, 8705 (2003); (http://dx.doi.org/10.1016/j.tetlet.2003.09.175)
3. (g). J. Chen, Q. Song, Z. Xi. Tetrahedron Lett. 43, 3533 (2002); (http://dx.doi.org/10.1016/S0040-4039(02)00581-6)
3. (h). J. Chen, Q. Song, P. Li, H. Guan, X. Jin, Z. Xi. Org. Lett. 4, 2269 (2002); (http://dx.doi.org/10.1021/ol0261478)
3. (i). Z. Xi, Q. Song, J. Chen, H. Guan, P. Li. Angew. Chem., Int. Ed. 40, 1913 (2001); (http://dx.doi.org/10.1002/1521-3773(20010518)40:10<1913::AID-ANIE1913>3.0.CO;2-N)
3. (j). Z. Xi, Q. Song. J. Org. Chem. 65, 9157 (2000). (http://dx.doi.org/10.1021/jo005641r)
4. Z. Xi. Bull. Chem. Soc. Jpn. 80, 1021 (2007). (http://dx.doi.org/10.1246/bcsj.80.1021)
5. L. S. Trzupek, T. L. Newirth, E. G. Kelly, N. E. Sbarbati, G. M. Whitesides. J. Am. Chem. Soc. 95, 8118 (1973). (http://dx.doi.org/10.1021/ja00805a028)
6. (a). N. S. Nudelman, A. A. Vitale. J. Org. Chem. 46, 4625 (1981); (http://dx.doi.org/10.1021/jo00335a080)
6. (b). N. S. Nudelman. "Carbonylation of main-group organometal compound", in The Chemistry of Double Bonded Functional Groups, S. Patai (Ed.), pp. 799-962, John Wiley, Chichester (1989).
7. (a). D. Seyferth, R. M. Weinstein. J. Am. Chem. Soc. 104, 5534 (1982); (http://dx.doi.org/10.1021/ja00384a065)
7. (b). D. Seyferth, R. C. Hui. J. Org. Chem. 50, 1985 (1985); (d) D. Seyferth, R. C. Hui, W.-L. Wang. J. Org. Chem. 58, 5843 (1993); (e) S. Murai, I. Ryu, J. Iriguchi, N. Sonoda. J. Am. Chem. Soc. 106, 2440 (1984). (http://dx.doi.org/10.1021/ja00320a039)
8. (a). I. Ryu, Y. Hayama, A. Hirai, N. Sonoda, A. Orita, K. Ohe, S. Murai. J. Am. Chem. Soc. 112, 7061 (1990); (http://dx.doi.org/10.1021/ja00175a051)
8. (b). H. Kai, K. Iwamoto, N. Chatani, S. Murai. J. Am. Chem. Soc. 118, 7634 (1996); (http://dx.doi.org/10.1021/ja961229a)
8. (c). K. Iwamoto, N. Chatani, S. Murai. J. Org. Chem. 65, 7944 (2000). (http://dx.doi.org/10.1021/jo000977m)
9. (a). K. Smith, G. J. Pritchard. Angew. Chem., Int. Ed. Engl. 29, 282 (1990); (http://dx.doi.org/10.1002/anie.199002821)
9. (b). K. Smith, G. A. ElHiti, G. J. Pritchard, A. Hamilton. J. Chem. Soc., Perkin Trans. 1 2299 (1999). (http://dx.doi.org/10.1039/a903467f)
10. T. Takahashi, S. Huo, R. Hara, Y. Noguchi, K. Nakajima, W. Sun. J. Am. Chem. Soc. 121, 1094 (1999). (http://dx.doi.org/10.1021/ja982570t)
11. Q. Song, Z. Li, J. Chen, C. Wang, Z. Xi. Org. Lett. 4, 4627 (2002). (http://dx.doi.org/10.1021/ol026977l)
12. (a). J. Barluenga, M. A. Fernandez-Rodriguez, E. Aguilar. J. Organomet. Chem. 690, 539 (2005); (http://dx.doi.org/10.1016/j.jorganchem.2004.10.032)
12. (b). M. Gomez-Gallego, M. J. Mancheno, M. A. Sierra. Acc. Chem. Res. 38, 44 (2005); (http://dx.doi.org/10.1021/ar040005r)
12. (c). Y. Zhao, J. Wang. Synlett 2886 (2005);
12. (d). J. Barluenga, J. Santamaria, M. Tomas. Chem. Rev. 104, 2259 (2004); (http://dx.doi.org/10.1021/cr0306079)
12. (e). K. H. Dotz, C. Jakel, W.-C. Haase. J. Organomet. Chem. 617/618, 119 (2001); (http://dx.doi.org/10.1016/S0022-328X(00)00650-1)
12. (f). J. Barluenga, J. Florez, F. J. Fananas. J. Organomet. Chem. 624, 5 (2001); (http://dx.doi.org/10.1016/S0022-328X(00)00837-8)
12. (g). M. A. Sierra. Chem. Rev. 100, 3591 (2000); (http://dx.doi.org/10.1021/cr9804137)
12. (h). A. de Meijere, H. Schirmer, M. Duetsch. Angew. Chem., Int. Ed. 39, 3964 (2000); (http://dx.doi.org/10.1002/1521-3773(20001117)39:22<3964::AID-ANIE3964>3.0.CO;2-C)
12. (i). J. Barluenga, F. J. Fananas. Tetrahedron 56, 4597 (2000); (http://dx.doi.org/10.1016/S0040-4020(00)00237-4)
12. (j). J. W. Herndon. Tetrahedron 56, 1257 (2000); (http://dx.doi.org/10.1016/S0040-4020(99)00981-3)
12. (k). R. Aumann. Eur. J. Org. Chem. 17 (2000); (http://dx.doi.org/10.1002/(SICI)1099-0690(200001)2000:1<17::AID-EJOC17>3.0.CO;2-T)
12. (l). E. O. Fischer, A. Maasbol. Angew. Chem., Int. Ed. Engl. 3, 580 (1964); (http://dx.doi.org/10.1002/anie.196405801)
12. (m). F. Glorius (Ed.). N-Heterocyclic Carbenes in Transition-Metal Catalysis, Topics in Organometallic Chemistry, Springer (2006);
12. (n). M. P. Doyle. J. Org. Chem. 71, 9253 (2006). (http://dx.doi.org/10.1021/jo061411m)
13. R. Aumann, K. Roths, B. Jasper, R. Frohlich. Organometallics 15, 1257 (1996). (http://dx.doi.org/10.1021/om950741m)
14. (a). H. P. Wu, R. Aumann, R. Frohlich, B. Wibbeling. Chem.Eur. J. 8, 910 (2002); (http://dx.doi.org/10.1002/1521-3765(20020215)8:4<910::AID-CHEM910>3.0.CO;2-T)
14. (b). N. Iwasawa, M. Shido, K. Maeyama, H. Kusama. J. Am. Chem. Soc. 122, 10226 (2000); (http://dx.doi.org/10.1021/ja001481p)
14. (c). H. Kusama, F. Shiozawa, M. Shido, N. Iwasawa. Chem. Lett. 124 (2002); (http://dx.doi.org/10.1246/cl.2002.124)
14. (d). S. L. B. Wang, W. D. Wulff. J. Am. Chem. Soc. 112, 4550 (1990). (http://dx.doi.org/10.1021/ja00167a067)
15. H. Kusama, T. Sawada, A. Okita, F. Shiozawa, N. Iwasawa. Org. Lett. 8, 1077 (2006). (http://dx.doi.org/10.1021/ol052951t)
16. Q. Wang, W.-X. Zhang, Z. Xi. Organometallics 27, 3627 (2008). (http://dx.doi.org/10.1021/om800565r)
17. (a). E. Licandro, S. Maiorana, A. Papagni, A. Zanotti Gerosa, F. Cariati, S. Bruni, M. Moret, A. Chiesi Villa. Inorg. Chim. Acta 220, 233 (1994); (http://dx.doi.org/10.1016/0020-1693(94)03875-9)
17. (b). D. Perdicchia, E. Licandro, S. Maiorana, B. Vandoni, C. Baldoli. Org. Lett. 4, 827 (2002). (http://dx.doi.org/10.1021/ol025504b)
18. Z. Zheng, J. Chen, Z. Yu, X. Han. J. Organomet. Chem. 691, 3679 (2006). (http://dx.doi.org/10.1016/j.jorganchem.2006.05.021)
19. E. O. Fischer, S. Walz, G. Kreis, F. R. Kreissl. Chem. Ber. 110, 1651 (1977). (http://dx.doi.org/10.1002/cber.19771100509)
20. Q. Song, J. Chen, X. Jin, Z. Xi. J. Am. Chem. Soc. 123, 10419 (2001). (http://dx.doi.org/10.1021/ja0165638)
21. (a). Z. Wang, H. Fang, Z. Xi. Tetrahedron 62, 6967 (2006); (http://dx.doi.org/10.1016/j.tet.2006.04.083)
21. (b). H. Fang, Q. Song, Z. Wang, Z. Xi. Tetrahedron Lett. 45, 5159 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.04.156)
22. (a). Z. Xi, W.-X. Zhang, Z. Song, W. Zheng, F. Kong, T. Takahashi. J. Org. Chem. 70, 8785 (2005); (http://dx.doi.org/10.1021/jo051178c)
22. (b). Z. Xi, W.-X. Zhang, T. Takahashi. Tetrahedron Lett. 45, 2427 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.01.098)
23. C. Wang, J. Chen, Q. Song, Z. Li, Z. Xi. Arkivoc part(ii), 155 (2003).
24. (a). G. D. Henry. Tetrahedron 60, 6043 (2004); (http://dx.doi.org/10.1016/j.tet.2004.04.043)
24. (b). G. R. Newkome, A. K. Patri, E. Holder, U. S. Schubert. Eur. J. Org. Chem. 235 (2004); (http://dx.doi.org/10.1002/ejoc.200300399)
24. (c). Z. Xi, Z. Li. Topic Organomet. Chem. 8, 27 (2004);
24. (d). F. Foubelo, M. Yus. Current. Org. Chem. 9, 459 (2005);
24. (e). P. Langer, W. Freiberg. Chem. Rev. 104, 4125 (2004); (http://dx.doi.org/10.1021/cr010203l)
24. (f). C. Najera, J. M. Sansano, M. Yus. Tetrahedron 59, 9255 (2003). (http://dx.doi.org/10.1016/j.tet.2003.09.065)
25. (a). T.-Y. Luh, C.-F. Lee. Eur. J. Org. Chem. 3875 (2005); (http://dx.doi.org/10.1002/ejoc.200500245)
25. (b). P. Mathew, C. V. Asokan. Tetrahedron 62, 1708 (2006); (http://dx.doi.org/10.1016/j.tet.2005.11.076)
25. (c). L. Lu, G. Chen, S. Ma. Org. Lett. 8, 835 (2006). (http://dx.doi.org/10.1021/ol052797a)
26. J. Chen, Q. Song, C. Wang, Z. Xi. J. Am. Chem. Soc. 124, 6238 (2002). (http://dx.doi.org/10.1021/ja0262176)
27. C. Wang, Z. Wang, L. Liu, C. Wang, G. Liu, Z. Xi. J. Org. Chem. 71, 8565 (2006). (http://dx.doi.org/10.1021/jo061574a)
28. S. Robin, G. Rousseau. Tetrahedron 54, 13681 (1998). (http://dx.doi.org/10.1016/S0040-4020(98)00698-X)
29. V. Blot, V. Reboul, P. Metzner. J. Org. Chem. 69, 1196 (2004). (http://dx.doi.org/10.1021/jo035488b)
30. (a). T. Yao, R. C. Larock. J. Org. Chem. 70, 1432 (2005); (http://dx.doi.org/10.1021/jo048007c)
30. (b). K. Cherry, J. Thibonnet, A. Duchene, J.-L. Parrain, M. Abarbri. Tetrahedron Lett. 45, 2063 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.01.063)
31. C. Wang, J. Lu, G. Mao, Z. Xi. J. Org. Chem. 70, 5150 (2005). (http://dx.doi.org/10.1021/jo050433q)
32. (a) J. Clayden. Organolithiums: Selectivity for Synthesis, Tetrahedron Organic Chemistry Series, Vol. 23, pp. 282-335, Pergamon, Oxford (2002).
33. (a). J. Clayden, F. E. Knowles, I. R. Baldwin. J. Am. Chem. Soc. 127, 2412 (2005); (http://dx.doi.org/10.1021/ja042415g)
33. (b). J. Clayden, R. Turnbull, I. Pinto. Org. Lett. 6, 609 (2004); (http://dx.doi.org/10.1021/ol0364071)
33. (c). J. Clayden, R. Turnbull, M. Helliwell, I. Pinto. Chem. Commun. 2430 (2004); (http://dx.doi.org/10.1039/b409150g)
33. (d). J. Clayden, M. N. Kenworthy. Synthesis 1721 (2004); (http://dx.doi.org/10.1055/s-2004-829138)
33. (e). J. Clayden. Organolithiums: Selectivity for Synthesis, Tetrahedron Organic Chemistry Series, Vol. 23, pp. 327-329, Pergamon, Oxford (2002).
34. J. Clayden, S. D. Hamilton, R. T. Mohammed. Org. Lett. 7, 3673 (2005). (http://dx.doi.org/10.1021/ol051214u)
35. (a). Z. Wang, Z. Xi. Synlett 1275 (2006);
35. (b). L. Liu, Z. Wang, F. Zhao, Z. Xi. J. Org. Chem. 72, 3484 (2007). (http://dx.doi.org/10.1021/jo070160u)

Pure and Applied Chemistry

Navigation

PAC Archives

RSS Feeds

Highlights

1-Lithio-1,3-dienes as useful building blocks in organic synthesis

References

Pure and Applied Chemistry

Navigation

Search PAC

PAC Archives

RSS Feeds

Highlights

1-Lithio-1,3-dienes as useful building blocks in organic synthesis

References