Prepration and reactions of acylzinc species

Tetrahedron

Volumn 53, Issue 51, 1997, Pages 17265-17274

  Chemla, F ^a   Normant, J F ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0030819701     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10179-X     Document Type: Article

References (42)

1. Narayana, C.; Periasamy, M. Synthesis 1985, 253-268. Nudelman N. Carbonylation of main-group organometallic compounds. In The chemistry of Double-bonded Fonctional Groups; Patai, S., Ed.; John Wiley & Sons Ltd: NewYork, 1989; pp. 799-962.
2. Narayana, C.; Periasamy, M. Synthesis 1985, 253-268. Nudelman N. Carbonylation of main-group organometallic compounds. In The chemistry of Double-bonded Fonctional Groups; Patai, S., Ed.; John Wiley & Sons Ltd: NewYork, 1989; pp. 799-962.
3. Seyferth, D.; Hui, R.C.; Wang, W.-L. J. Org. Chem. 1993, 58, 5843; Seyferth, D.; Weistein, R.M.; Hui, R.C.; Wang, W.-L.; Archer, C.M. J. Org. Chem. 1992, 57, 5620;; Seyferth, D.; Weistein, R.M.; Hui, R.C.; Wang, W.-L.; Archer, C.M. J. Org. Chem. 1991, 56, 5768.
4. Seyferth, D.; Hui, R.C.; Wang, W.-L. J. Org. Chem. 1993, 58, 5843; Seyferth, D.; Weistein, R.M.; Hui, R.C.; Wang, W.-L.; Archer, C.M. J. Org. Chem. 1992, 57, 5620;; Seyferth, D.; Weistein, R.M.; Hui, R.C.; Wang, W.-L.; Archer, C.M. J. Org. Chem. 1991, 56, 5768.
5. Seyferth, D.; Hui, R.C.; Wang, W.-L. J. Org. Chem. 1993, 58, 5843; Seyferth, D.; Weistein, R.M.; Hui, R.C.; Wang, W.-L.; Archer, C.M. J. Org. Chem. 1992, 57, 5620;; Seyferth, D.; Weistein, R.M.; Hui, R.C.; Wang, W.-L.; Archer, C.M. J. Org. Chem. 1991, 56, 5768.
6. Kabalka, G.W.; Li, N.-S.; Yu, S. Organometallics 1995, 14, 1565-1566; Li, N.-S.; Yu, S.; Kabalka, G.W. J. Org. Chem. 1995, 60, 5973-5974; Kabalka, G.W.; Gotsick, J.T.; Pace, R.D.; Li, N.-S. Organometallics 1994, 13, 5163-5165.
7. Kabalka, G.W.; Li, N.-S.; Yu, S. Organometallics 1995, 14, 1565-1566; Li, N.-S.; Yu, S.; Kabalka, G.W. J. Org. Chem. 1995, 60, 5973-5974; Kabalka, G.W.; Gotsick, J.T.; Pace, R.D.; Li, N.-S. Organometallics 1994, 13, 5163-5165.
8. Kabalka, G.W.; Li, N.-S.; Yu, S. Organometallics 1995, 14, 1565-1566; Li, N.-S.; Yu, S.; Kabalka, G.W. J. Org. Chem. 1995, 60, 5973-5974; Kabalka, G.W.; Gotsick, J.T.; Pace, R.D.; Li, N.-S. Organometallics 1994, 13, 5163-5165.
9. Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459-5461; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533-1536; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477-481; Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061-7063.
10. Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459-5461; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533-1536; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477-481; Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061-7063.
11. Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459-5461; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533-1536; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477-481; Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061-7063.
12. Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459-5461; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533-1536; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477-481; Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061-7063.
13. Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459-5461; Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635; Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533-1536; Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477-481; Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061-7063.
14. Smith, K.; Pritchard, G.J. Angew. Chem. Int. Ed. Engl. 1990, 29, 282-283.
15. Wheeler, O.H. Reduction. In The Chemistry of Acyl Halides; Patai, S., Ed.; John Wiley & Sons: New York, 1972; pp.231-251.
16. Fischer, F.G.; Stoffers, O. J. Liebigs. Ann. Chem. 1933, 500, 253.
17. Rathke, M.W.; Yu, H. J. Org. Chem. 1972, 37, 1732-1734.
18. Jackson, R.F.W.; Turner, D.; Block, M.H. J. Chem. Soc., Perkin Trans. I 1997, 865-870.
19. Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 8411-8414.
20. Pospekliov, D.A. Khim. Referat. Zhur. 1941, 4, 30; Chem. Abstr. 1943, 37, 4359.
21. Pospekliov, D.A. Khim. Referat. Zhur. 1941, 4, 30; Chem. Abstr. 1943, 37, 4359.
22. Varvoglis, G.A. Chem. Ber. 1937, 70, 2391-2396.
23. Bhar, S.; Ranu, B.C. J. Org. Chem. 1995, 60, 745-747.
24. Chemla, F.; Normant, J. Synth. Commun. 1997, submitted.
25. Vedejs, E. Org. React. 1974, 22, 401-422. Motherwell, W.B.; Nutley, C.J. Contemp. Org. Synth. 1995, 1, 219-241.
26. Vedejs, E. Org. React. 1974, 22, 401-422. Motherwell, W.B.; Nutley, C.J. Contemp. Org. Synth. 1995, 1, 219-241.
27. We thank Pr. M. Julia for having proposed this alternate explanation.
28. Schaefer III, H.F. Acc. Chem. Res 1979, 12, 288-297. Nickon, A. Acc. Chem. Res. 1993, 26, 84-89. Sulzbach, H.M.; Platz, M.S.; Schaefer III, H.F.; Hadad, C.M. J. Am. Chem. Soc. 1997, 119, 5682-5689.
29. Schaefer III, H.F. Acc. Chem. Res 1979, 12, 288-297. Nickon, A. Acc. Chem. Res. 1993, 26, 84-89. Sulzbach, H.M.; Platz, M.S.; Schaefer III, H.F.; Hadad, C.M. J. Am. Chem. Soc. 1997, 119, 5682-5689.
30. Schaefer III, H.F. Acc. Chem. Res 1979, 12, 288-297. Nickon, A. Acc. Chem. Res. 1993, 26, 84-89. Sulzbach, H.M.; Platz, M.S.; Schaefer III, H.F.; Hadad, C.M. J. Am. Chem. Soc. 1997, 119, 5682-5689.
31. Agosta, W.C.; Foster, A.M. J. Chem. Soc., Chem. Commun. 1971, 433-434. Moss, R.A.; Xue, S.; Liu, W.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1996, 118, 12588-12597.
32. Agosta, W.C.; Foster, A.M. J. Chem. Soc., Chem. Commun. 1971, 433-434. Moss, R.A.; Xue, S.; Liu, W.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1996, 118, 12588-12597.
33. The reason of this Z-exclusive stereodirection could also possibly be attributed to (E) to (Z) zinc enolate equilibration. However, from the best of our knowledge, nothing to date is known about the (E)-(Z) zinc aldehyde enolates equilibration in ethyl acetate.
34. Tomioka, H.; Sugiura, T.; Masumoto, Y.; Izawa, Y.; Inagaki, S.; Iwase, K. J. Chem. Soc., Chem. Commun. 1986, 693-695.
35. Bruneau, C.; Dixneuf, P.H. J. Chem. Soc., Chem. Commun. 1997, 507-512 and ref. cit.
36. Larock, R.C.; Oertle, K.; Beatty, K.M. J. Am. Chem. Soc. 1980, 102, 1966-1974 and ref. cit.
37. Kita, Y.; Akai, S.; Ajimura, N.; Yoshigi, M.; Tsugoshi, T.; Yasuda, H.; Tamura, Y. J. Org. Chem. 1986, 51, 4150-4158.
38. Kowalski, C.J.; Haque, M.S. J. Am. Chem. Soc. 1986, 108, 1325-1327.
39. Hudrlik, P.P.; Hudrlik, A.M.; Rona, R.J.; Misra, R.N.; Withers, G.P. J. Am. Chem. Soc 1977, 99, 1993-1996.
40. Söderberg, B.C.; Turbeville, M.J. Organometallics 1991, 10, 3951-3953.
41. Doucet, H.; Martin-Vaca, B.; Bruneau, C.; Dixneuf, P.H. J. Org. Chem. 1995, 60, 7247-7255.
42. Knochel, P.; Singer, R.D. Chem. Rev. 1993, 93, 2117-2188.