Highly stereoselective synthesis of homoallylic amines based on addition of allyltrichlorosilanes to benzoylhydrazones under neutral conditions [4]

Journal of the American Chemical Society

Volumn 121, Issue 29, 1999, Pages 6942-6943

  Kobayashi, Shu ^a   Hirabayashi, Ryoji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HYDRAZONE DERIVATIVE; SILANE DERIVATIVE;

DIASTEREOISOMER; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033612727     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990497g     Document Type: Letter

References (30)

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20. Cf. (c) Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266.
21. 2, and THF, whereas no addition to aldehydes occurred in these solvents. See refs 4a and b.
22. It is noted that solubility in solvents other than DMF, HMPA, and DMA was inadequate.
23. Synthesis of (Z)-isomer, see: (a) Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081. (b) Kira, M.; Hino, T.; Sakurai, H. Tetrahedron Lett. 1989, 30, 1099. (E)-isomer, see: (c) Furuya, N.; Sukawa, T. J. Organomet. Chem. 1975, 96, C1.
24. Synthesis of (Z)-isomer, see: (a) Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081. (b) Kira, M.; Hino, T.; Sakurai, H. Tetrahedron Lett. 1989, 30, 1099. (E)-isomer, see: (c) Furuya, N.; Sukawa, T. J. Organomet. Chem. 1975, 96, C1.
25. Synthesis of (Z)-isomer, see: (a) Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081. (b) Kira, M.; Hino, T.; Sakurai, H. Tetrahedron Lett. 1989, 30, 1099. (E)-isomer, see: (c) Furuya, N.; Sukawa, T. J. Organomet. Chem. 1975, 96, C1.
26. syn and anti configuration was determined after converting to the corresponding amine. See Supporting Information.
27. 2NEt to neutralize the acid.
28. Relative configuration assignment was performed after converting to the corresponding amine. See Supporting Information.
29. Nitrogen-nitrogen bonds can be also cleavaged under other reductive conditions. For examples, see refs 5a and b.
30. 3b