Enantioselective synthesis of non-proteinogenic 2-arylallyl-α-amino acids via Pd/In catalytic cascades

Tetrahedron

Volumn 62, Issue 52, 2006, Pages 12159-12171

  Grigg, Ronald ^a   McCaffrey, Shaun ^a   Sridharan, Visuvanathar ^a   Fishwick, Colin W G ^a   Kilner, Colin ^a   Korn, Stewart ^b   Bailey, Kevin ^b   Blacker, John ^b  

^a School of Chemistry University of Leeds Woodhouse Lane   (United Kingdom)

^b Avecia Biologics Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 AMINO) 4 (3 METHOXYPHENYL)PENT 4 ENOIC ACID; 2 (2 AMINO) 4 (3,4 DICHLOROPHENYL)PENT 4 ENOIC ACID; 2 (2 AMINO) 4 (3,5 BISTRIFLUOROMETHYLPHENYL)PENT 4 ENOIC ACID; 2 (2 AMINO) 4 (4 TOLYL)PENT 4 ENOIC ACID; 2 (2 AMINO) 4 (4 TRIFLUOROMETHYLPHENYL)PENT 4 ENOIC ACID; 2 (2 AMINO) 4 (6 CHLOROPYRIDIN 2 YL)PENT 4 ENOIC ACID; 2 (2 AMINO) 4 PHENYLPENT 4 ENOIC ACID; AMINO ACID DERIVATIVE; INDIUM; PALLADIUM; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 33750945878     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.098     Document Type: Article

References (18)

1. Najera C. Synlett (2002) 1388-1403
2. Hohsaka T., and Sisido M. Curr. Opin. Chem. Biol. 6 (2002) 809-815
3. Hodgson D.R.W., and Sanderson J.M. Chem. Soc. Rev. 33 (2004) 422-430
4. Anwar U., Grigg R., and Sridharan V. Chem. Commun. (2000) 933-934
5. Anwar U., Grigg R., Rasparini M., Savic V., and Sridharan V. Chem. Commun. (2000) 645-646
6. Cleghorn L.A.T., Cooper I.R., Fishwick C.W.G., Grigg R., MacLachlan W.S., Rasparini M., and Sridharan V. J. Organomet. Chem. 687 (2003) 483-493
7. Cleghorn L.A.T., Cooper I.R., Grigg R., MacLachlan W.S., and Sridharan V. Tetrahedron Lett. 44 (2003) 7969-7973
8. Cooper I.R., Grigg R., MacLachlan W.S., Sridharan V., and Thornton-Pett M. Tetrahedron Lett. 44 (2002) 403-405
9. Cooper I.R., Grigg R., MacLachlan W.S., Thornton-Pett M., and Sridharan V. Chem. Commun. (2002) 1372-1373
10. Cooper I.R., Grigg R., Hardie M.J., MacLachlan W.S., Sridharan V., and Thomas W.A. Tetrahedron Lett. 44 (2003) 2283-2285
11. Ellman J.A., Owens T.D., and Tang T.P. Acc. Chem. Res. 35 (2002) 984-995
12. Ellman J.A. Pure Appl. Chem. 75 (2003) 39-46
13. Davis F.A., Lee S., Zhang H., and Fanelli D.L. J. Org. Chem. 65 (2000) 8704-8708
14. Evans J.W., and Ellman J.A. J. Org. Chem. 68 (2003) 9948-9957
15. Supplementary crystallographic data for S,S-6 (CCDC 277090), R,R-6 (CCDC 277091) and R,R,S-18 (CCDC 277092) can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif.
16. Semi-empirical calculations were performed using MOPAC v7 by J. J. P. Stewart and the PM3 Hamiltonian. Approximate transition structures were located using the SADDLE routine within MOPAC following full conformational optimisation of the attached sub-structures (MM2). Transition structures were then fully optimised using the TS routine within MOPAC and these then characterised by observing them to have a single negative vibrational frequency following use of the FORCE calculation within MOPAC.
17. Grigg R., and Sridharan V. In: Davies S.G., and Murahashi S.-I. (Eds). Transition Metal Catalysed Reactions. IUPAC Monograph (1999), Blackwell Science 81-97
18. Grigg R., and Sridharan V. In: Tsuji J. (Ed). Perspectives in Organopalladium Chemistry for the 21st Century (1989), Elsevier 65-87