A convenient cross-coupling route to α,β,γ,δ-unsaturated amino acids

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1309-1312

  Burk, Mark J ^a   Allen, John G ^a   Kiesman, William F ^a   Stoffan, Karen M ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; ISOMERISM; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00065-8     Document Type: Article

References (23)

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2. 1. Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53-61; Schmidt, O.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159-172; Nunami, K.; Hiramatsu, K.; Hayashi, K.; Matsumoto, K. Tetrahedron 1988, 44, 5467-5478; Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487-490.
3. 1. Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53-61; Schmidt, O.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159-172; Nunami, K.; Hiramatsu, K.; Hayashi, K.; Matsumoto, K. Tetrahedron 1988, 44, 5467-5478; Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487-490.
4. 1. Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53-61; Schmidt, O.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159-172; Nunami, K.; Hiramatsu, K.; Hayashi, K.; Matsumoto, K. Tetrahedron 1988, 44, 5467-5478; Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487-490.
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8. 4. Jung, G. Angew. Chem. Int. Ed. Engl. 1991, 30, 1051-1068; Freud, S.; Jung, G.; Gutbrod, O.; Folkers, G.; Gibbons, W. A.; Allgaier, H.; Werner, R. Biopolymers 1991, 31, 803-811.
9. 5. Burk, M. J.; Gross, M. F.; Harper, T. G. P.; Kalberg, C. S.; Lee, J. R.; Martinez, J. P. Pure & Appl. Chem. 1996, 68, 37-44 and references cited therein.
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13. 7. Suzuki, A. Pure & Appl. Chem. 1985, 57, 1749-1758; Suzuki, A. Pure & Appl. Chem. 1991, 63, 419-422; Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, G. M. J. Chem. Soc., Chem. Commun. 1994, 2395.
14. 8. Danion-Bougot, R.; Danion, D.; Francis, G. Tetrahedron Lett. 1990, 31, 3739-3742.
15. 2, 1:1 EtOAc/PE).
16. 10. Representative NOE experiments on examples of starting materials and products: (formula presented)
17. 11. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4370-4371; Lane, C. F.; Kabalka, G. W. Tetrahedron 1976, 32, 981-990.
18. 11. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4370-4371; Lane, C. F.; Kabalka, G. W. Tetrahedron 1976, 32, 981-990.
19. 12. The boronic acids were all colorless crystalline solids which in vacuo became oily semisolids.
20. +) 281.1991.
21. 14. Preliminary work at 70 °C with the catalyst system described in Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847 gave mixtures of E and Z products.
22. 15. Extended reaction times (>24 h) under these conditions lead to isomerization of the product.
23. 16. Hegedus, L. S.; Palladium in Organic Synthesis. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; Chapter 5.