A straightforward synthetic approach to β-substituted phenylalanines via ring opening of aryl epoxides

Synthesis

Volumn , Issue 7, 2011, Pages 1059-1066

  Zahoor, Ameer F ^a   Kazmaier, Uli ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

amino acids; chelated enolates; epoxide openings; epoxides; phenylalanine derivatives

Indexed keywords

AMINO ACID ESTERS; CHELATED ENOLATES; ENOLATES; EPOXIDE OPENINGS; EPOXIDES; PHENYLALANINE DERIVATIVES; REGIOSELECTIVE RING OPENING; RING OPENING; SYNTHETIC APPROACH;

CHELATION; ESTERS; METHANOL;

AMINO ACIDS;

2,2,2 TRIFLUORO N [(SYN) 2 OXO 4 PHENYLTETRAHYDROFURAN 3 YL]ACETAMIDE; ARYL EPOXIDE; CHEMICAL COMPOUND; EPOXIDE; PHENYLALANINE DERIVATIVE; TERT BUTYL 3 (2 CHOLOROPHENYL) 4 HYDROXY 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 3 (2 CHOLOROPHENYL) 4 OXO 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 3 (3,4 DICHOLOROPHENYL) 4 HYDROXY 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 3 (4 BROMOPHENYL) 4 HYDROXY 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 3 (4 CHOLOROPHENYL) 4 HYDROXY 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 3 (4 CHOLOROPHENYL) 4 OXO 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 (METHYLSULFONYLOXY) 3 PHENYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 (METHYLTHIOCARBONOTHIOYLOXY) 3 PHENYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 AMINO 3 PHENYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 AZIDO 3 PHENYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 HYDROXY 3 (2 METHOXYPHENYL) 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 HYDROXY 3 (4 METHOXYPHENYL) 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 HYDROXY 3 (NAPHTHALEN 2 YL) 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 HYDROXY 3 3 TOLYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 HYDROXY 3 4 TOLYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 HYDROXY 3 PHENYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 OXO 3 3 TOLYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 OXO 3 4 TOLYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 4 OXO 3 PHENYL 2 (2,2,2 TRIFLUOROACETAMIDO)BUTANOATE; TERT BUTYL 5,5 DIBROMO 3 PHENYL 2 (2,2,2 TRIFLUOROACETAMIDO)PENT 4 ENOATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; LACTONIZATION; MICHAEL ADDITION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; TEMPERATURE;

EID: 79953028236     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258460     Document Type: Article

References (50)

1. Schipper D, J. Antibiot. 1983 36 1076
2. Kazmierski W M., Yamamura H I., Hruby V J., J. Am. Chem. Soc. 1991 113 2275
3. Holladay M W., Nadzan A M., J. Org. Chem. 1991 56 3900
4. Kazmierski W M., Urbanczyk-Lipkowska Z, Hruby V J., J. Org. Chem. 1994 59 1789
5. Cardillo G, Gentilucci L, Tolomelli A, Mini-Rev. Med. Chem. 2006 5 293
6. For reviews, see:, Abellán T, Chinchilla R, Galindo N, Guillena G, Nájera C, Sansano J M., Eur. J. Org. Chem. 2000 2689
7. Ma J.-A, Angew. Chem. Int. Ed. 2003 42 4290; Angew. Chem. 2003, 115, 4426
8. Maruoka K, Ooi T, Chem. Rev. 2003 103 3013
9. Aurelio L, Brownlee R T. C., Hughes A B., Chem. Rev. 2004 104 5823
10. Ager D J., Laneman S A., In Asymmetric Catalysis on Industrial Scale Blaser H U. Schmidt E Wiley-VCH Weinheim 2004 259
11. Najera C, Sansano J M., Chem. Rev. 2007 107 4584
12. Michaux J, Niel G, Campagne J.-M, Chem. Soc. Rev. 2009 38 2093
13. Kazmaier U, Amino Acids 1996 11 283
14. Deska J, Kazmaier U, Curr. Org. Chem. 2008 12 7355
15. Kazmaier U, In Frontiers in Asymmetric Synthesis and Application of alpha -Amino Acids Soloshonok V A. Izawa K ACS Books Washington 2009 157; and references cited therein
16. Kazmaier U, Grandel R, Synlett 1995 945
17. Grandel R, Kazmaier U, Nuber B, Liebigs Ann. 1996 1143
18. Grandel R, Kazmaier U, Rominger F, J. Org. Chem. 1998 63 4524
19. Pohlman M, Kazmaier U, Org. Lett. 2003 5 2631
20. Pohlman M, Kazmaier U, Lindner T, J. Org. Chem. 2004 69 6909
21. Schmidt C, Kazmaier U, Eur. J. Org. Chem. 2008 887
22. Kazmaier U, Curr. Org. Chem. 2003 317
23. Kazmaier U, Pohlman M, Synlett 2004 623
24. Kazmaier U, Lindner T, Angew. Chem. Int. Ed. 2005 44 3303;
25. Angew. Chem. 2005, 117, 3368
26. Krebs A, Kazmaier U, Tetrahedron Lett. 1996 37 7945
27. Kazmaier U, Liebigs Ann./Recl. 1997 285
28. Mues H, Kazmaier U, Synthesis 2001 487
29. Kazmaier U, Mues H, Krebs A, Chem. Eur. J. 2002 8 1850
30. Quirin C, Kazmaier U, Synthesis 2009 1725
31. Kazmaier U, Stolz D, Angew. Chem. Int. Ed. 2006 45 3072;
32. Angew. Chem. 2006, 118, 3143
33. Kazmaier U, Zumpe F L., Eur. J. Org. Chem. 2001 4067
34. Kazmaier U, Stolz D, Krämer K, Zumpe F L., Chem. Eur. J. 2008 14 1322
35. Mendler B, Kazmaier U, Synthesis 2005 2239
36. Mendler B, Kazmaier U, Org. Lett. 2005 7 1715
37. Kazmaier U, Zahoor A F., ARKIVOC 2011 in press
38. Smith A B., Jerris P J., J. Am. Chem. Soc. 1981 103 194
39. Ghribi A, Alexakis A, Normant J F., Tetrahedron Lett. 1984 25 3075
40. Eis M J., Ganem B, Tetrahedron Lett. 1985 26 1153
41. Alexakis A, Jachiet D, Normant J F., Tetrahedron 1986 42 5607
42. Burk M J., Lee J R., Martinez J P., J. Am. Chem. Soc. 1994 116 10847
43. DeVasher R B., Moore L R., Shaughnessy K H., J. Org. Chem. 2004 69 7919
44. Kainmueller E K., Bannwarth W, Helv. Chim. Acta 2006 89 3056
45. Maslak V, Matovi R, Saii R N., Tetrahedron Lett. 2002 43 5411
46. Meulemans T M., Stork G A., Macaev F Z., Jansen B J. M., Groot A, J. Org. Chem. 1999 64 9178
47. Brémond P, Audran G, Monti H, Clercq E D., Pannecouque C, Synthesis 2009 290
48. Flohr A, Aemissegger A, Hilvert D, J. Med. Chem. 1999 42 2633
49. Lévêque L, Blanc M L., Pastor R, Tetrahedron Lett. 1998 39 8857
50. Bitar A Y., Frontier A J., Org. Lett. 2009 11 49