Heck reaction of amino acid derived vinyl substrates in the synthesis of homotyrosinol derivatives

Synthesis

Volumn , Issue 15, 2010, Pages 2515-2520

  Liang, Huan ^a   Zhou, Yuan ^a   Ciufolini, Marco A ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

coupling; Heck reaction; homotyrosine; N phenylurea; palladium

Indexed keywords

4-IODOPHENYL; HECK COUPLING; HECK REACTIONS; HOMOTYROSINE; N -PHENYLUREA; PHENYLUREAS;

AMINO ACIDS; ORGANIC ACIDS; PALLADIUM;

SYNTHESIS (CHEMICAL);

CARBANILAMIDE; TYROSINE DERIVATIVE; VINYL DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CATALYST; HECK REACTION;

EID: 77954901982     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218830     Document Type: Article

References (32)

1. (a) Ciufolini M A., Braun N A., Canesi S, Ousmer M, Chang J, Chai D, Synthesis 2007 3759
2. (b) Mendelsohn B A., Ciufolini M A., Org. Lett. 2009 11 4736
3. (c) Liang H, Ciufolini M A., [nl]J. Org. Chem. 2008 73 4299
4. (d) Frie J L., Jeffrey C S., Sorensen E J., Org. Lett. 2009 11 5394
5. (e) Sabot C, Guerard K C., Canesi S, Chem. Commun. 2009 2941
6. Canesi S, Bouchu D, Ciufolini M A., Angew. Chem. Int. Ed. 2004 43 4336
7. Suhartono M, Weidlich M, Stein T, Karas M, Dürner G, Göbel M W., Eur. J. Org. Chem. 2008 1608
8. Readily available from methionine, see:, Afzaliardakani A, Rapoport H, J. Org. Chem. 1980 45 4817
9. Krebs A, Ludwig V, Prizer J, Durner G, Gobel M W., Chem. Eur. J. 2004 10 544
10. (a) Heck R F., Nolley J P. Jr., J. Org. Chem. 1972 37 2320
11. (b) Heck R F., Org. React. 1989 27 345
12. (c) Beletskaya I, Cheprakov A, Chem. Rev. 2000 100 3009
13. (d) Littke A F., Fu G C., Angew. Chem. Int. Ed. 2002 41 4176
14. (e) Braese S, deMeijere A, Cross-coupling of organic halides with alkenes: The Heck reaction, In Metal-Catalyzed Cross-Coupling Reactions Diederich F Stang P J. Wiley-VCH Weinheim 2004
15. (a) Grubbs R H., Handbook of Metathesis Wiley-VCH Weinheim 2003
16. (b) Grubbs R H., Trnka T M., Ruthenium-Catalyzed Olefin Metathesis, In Ruthenium in Organic Synthesis Murahashi S.-I Wiley-VCH Germany 2004
17. (c) Trnka T M., Grubbs R H., Acc. Chem. Res. 2000 34 18
18. For a review, see:, Miyaura N, Suzuki A, Chem. Rev. 1995 95 2457
19. Collier P N., Campbell A D., Patel I, Raynham T M., Taylor R J. K., J. Org. Chem. 2002 67 1802
20. (a) Osborn J A., Jardine F H., Young J F., Wilkinson G, J. Chem. Soc. A 1966 1711
21. (b) Mannig D, Noth H, Angew. Chem. Int. Ed. 1985 24 878
22. Scholl M, Ding S, Lee C W., Grubbs R H., Org. Lett. 1999 1 953
23. Garber S B., Kingsbury J S., Gray B L., Hoveyda A H., J. Am. Chem. Soc. 2000 122 8168
24. (a) Schwab P, France M B., Ziller J W., Grubbs R H., Angew. Chem. Int. Ed. 1995 34 2039
25. (b) Schwab P, Grubbs R H., Ziller J W., J. Am. Chem. Soc. 1996 118 100
26. (c) Kingsbury J S., Harrity J P. A., Bonitatebus P J., Hoveyda A H., J. Am. Chem. Soc. 1999 121 791
27. Barder T E., Walker S D., Martinelli J R., Buchwald S L., J. Am. Chem. Soc. 2005 127 4685
28. (a) Cui X, Zhou Y, Wang N, Liu L, Guo Q X., Tetrahedron Lett. 2007 48 163
29. (b) Cui X, Li J, Fu Y, Liu L, Guo Q X., Tetrahedron Lett. 2008 49 3458
30. (a) Dale J A., Mosher H S., J. Am. Chem. Soc. 1973 95 512
31. (b) For a review, see:, Kusumi T, Ooi T, Ohkubo Y, Yabuuchi T, Bull. Chem. Soc. Jpn. 2006 79 965
32. Battace A, Zair T, Doucet H, Santelli M, Synthesis 2006 3495