Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates

Tetrahedron Letters

Volumn 46, Issue 43, 2005, Pages 7389-7392

  Poulsen, Sally Ann ^a   Bornaghi, Laurent F ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

Amino acids; Cross metathesis; Microwave; N Allylation; Olefin

Indexed keywords

ALKENE; AMINO ACID; DIMER;

ACCELERATION; ARTICLE; CHEMICAL REACTION; CROSS METATHESIS REACTION; MICROWAVE RADIATION;

EID: 25444458314     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.126     Document Type: Article

References (17)

1. R.H. Grubbs, and S. Chang Tetrahedron 54 1998 4413
2. R.H. Grubbs Tetrahedron 60 2004 7117
3. A.K. Chatterjee, T.-L. Choi, D.P. Sanders, and R.H. Grubbs J. Am. Chem. Soc. 125 2003 11360
4. W.R. Bowman, and D.R. Coghlan Tetrahedron 53 1997 15787
5. J.F. Reichwein, and R.M.J. Liskamp Tetrahedron Lett. 39 1998 1243
6. J.F. Reichwein, and R.M.J. Liskamp Eur. J. Org. Chem. 2000 2335
7. L.F. Bornaghi, S.-A. Poulsen, and P.C. Healy Acta Crystallogr. E60 2004 o383
8. S.-A. Poulsen, C.L. Noack, and P.C. Healy Acta Crystallogr. E59 2003 o967
9. +: 276.1594.
10. +: 551.3115.
11. S.C.G. Biagini, S.E. Gibson, and S.P. Keen J. Chem. Soc., Perkin Trans. 1 1998 2485
12. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953
13. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250
14. B.L. Hayes Aldrichim. Acta 37 2004 66
15. S.G. Aitken, and A.D. Abell Aust. J. Chem. 58 2005 3
16. S.S. Salim, R.K. Bellingham, and R.C.D. Brown Eur. J. Org. Chem. 2004 800
17. General experimental procedure for microwave accelerated CM: All reactions were carried out in a pressure tube, sealed with a Teflon septum. Reactions contained the N-allyl amino acid substrate 2a-c (0.1-0.2 mmol) and Grubbs second-generation catalyst (5-20%) in 1,2-DCE (0.8 mL). The pressure tube was introduced to the centre of a CEM Discover microwave oven and then heated to 100°C for 10 min. On completion of the heating cycle, the reaction mixture was purified and characterised in a manner identical to that described in Ref. 5. Yields: 3a 48%, 3b 54%, 3c 40%.