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In-Depth Information
formation, reactions proceeding with good selectivity. Amino alcohol derivatives
8.547
were formed as, pre-
dominantly, the
syn
isomer (Scheme 8.151), while diamine derivatives
8.550
tended to be
anti
(Scheme 8.152).
Insertion into tertiary CH bonds proceeded with retention of stereochemistry (Scheme 8.153).
177
The hetero-
cyclic products undergo useful nucleophilic ring opening (Scheme 8.151).
178
BothC-H insertion by a carbene andC-H insertion by a nitrenewere employed in a synthesis of tetrodotoxin
8.557
, the highly toxic alkaloid of the fugu fish (Scheme 8.154).
179
References
1. Aumann, R.; Fischer, E. O.
Chem. Ber.
1968
,
101
, 954.
2. Dotz, K. H.
Angew. Chem., Int. Ed. Engl.
1984
,
23
, 587.
3. Dotz, K. H.; Stendel, J.
Chem. Rev.
2009
,
109
, 3227
4. (a) Barluenga, J.; Fernandez-Rodrıguez, M. A.; Aguilar, E.
J. Organomet. Chem.
2005
,
690
, 539; (b) de Meijere,
A.
Pure Appl. Chem.
1996
,
68
, 61.
5. Hoye, T. R.; Chen, K.; Vyvyan, J. R.
Organometallics
1993
,
12
, 2806.
6. Wulff, W. D.; Yang, D. C.
J. Am. Chem. Soc.
1983
,
105
, 6726.
7. Aumann, R.; Hinterding, P.
et al. J. Organomet. Chem.
1993
,
459
, 145.
8. Bernasconi, C. F.; Sun, W.
Organometallics
1997
,
16
, 1926;
9. Bernasconi, C. F.; Leyes, A. E.
et al. J. Am. Chem. Soc.
1998
,
120
, 8632.
10. (a) Casey, C. P.; Boggs, R. A.; Anderson, R. L.
J. Am. Chem. Soc.
1972
,
94
, 8947; (b) Casey, C. P.; Anderson,
R. L.
J. Organomet. Chem.
1974
,
73
, C28.
11. (a) Aumann, R.; Heinen, H.
Chem. Ber.
1987
,
120
, 537; (b) Casey, C. P.; Brunsvold, W. R.
J. Organomet. Chem.
1975
,
102
, 175.
12. Soderberg, B. C.; Lin, J.
J. Org. Chem.
1997
,
62
, 5945.
13. Dotz, K. H.; Tomuschat, P.
Chem. Soc. Rev.
1999
,
28
, 187.
14. (a) Chamberlin, S.; Wulff, W. D.
et al. J. Am. Chem. Soc.
1992
,
114
, 10667; (b) Chamberlin, S.; Wulff, W. D.; Bax,
B.
Tetrahedron
1993
,
49
, 5531.
15. Yamashita, A.; Scahill, T. A.
J. Org. Chem.
1989
,
54
, 3625.
16. Semmelhack, M. F.; Bozell, J. J.
Tetrahedron
1985
,
41
, 5803.
17. Wulff, W. D.; Tang, P. C.
J. Am. Chem. Soc.
1984
,
106
, 434.
18. Dotz, K. H.; Popall, M.
Angew. Chem., Int. Ed. Engl.
1987
,
26
, 1158
19. Dotz, K. H.; Popall, M.
Tetrahedron
1985
,
41
, 5797
20. Mahlau, M.; Fernandes, R. A.; Bruckner, R.
Eur. J. Org. Chem.
2011
, 4765.
21. Semmelhack, M. F.; Bozell, J. J.
et al. J. Am. Chem. Soc.
1982
,
104
, 5850.
22. Yamashita, A.; Toy, A.
Tetrahedron Lett.
1986
,
27
, 3471.
23. (a) Brandvold, T. A.; Wulff, W. D.; Rheingold, A. L.
J. Am. Chem. Soc.
1990
,
112
, 1645; (b) Brandvold, T. A.;
Wulff, W. D.; Rheingold, A. L.
J. Am. Chem. Soc.
1991
,
113
, 5459; (c) Walters, M. L.; Brandvold, T. A.
et al.
Organomet.
1998
,
17
, 4298.
24. Wulff, W. D.; Kaessler, R. W.
Organometallics
,
1985
,
4
, 1461.
25. Ishibashi, T.; Ochifuji, N.; Mori, M.
Tetrahedron Lett.
1996
,
37
, 6165.
26. Challoner, C. A.; Wulff, W. D.
et al. J. Am. Chem. Soc.
1993
,
115
, 1359.
27. (a) Kim, O. K.; Wulff, W. D.
etal.J.Org.Chem.
1993
,
58
, 5571; (b) Jiang, W.; Fuertes, M. J.; Wulff, W. D.
Tetrahedron
2000
,
56
, 2183.
28. Parlier, A.; Rudler, H.
et al. J. Organomet. Chem.
1985
,
287
,C8.
29. Hoye, T. R.; Vyvyan, J. R.
J. Org. Chem.
1995
,
60
, 4184.
30. (a) Herndon, J. W.; Tumer, S. U.; Schnatter, W. F. K.
J. Am. Chem. Soc.
1988
,
110
, 3334; (b) Herndon, J. W.;
Chatterjee, G.
et al. J. Am. Chem. Soc.
1991
,
113
, 7808; (c) Tumer, S. U.; Herndon, J. W.; McMullen, L. A.
J. Am.
Chem. Soc.
1992
,
114
, 8394.
31. (a) Hegedus, L. S.
Tetrahedron
1997
,
53
, 4105; (b) Hegedus, L. S.; Schultze, L. M.
et al. Phil. Trans. R. Soc. Lond.
1988
,
A326
, 505.
