Synthesis of β,β′-diamino acids from α-amino acid-derived β-lactams by ring opening with nucleophiles. Utilization in the synthesis of peptidomimetics

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8659-8667

  Taubinger, Alexander A ^a   Fenske, Dieter ^a   Podlech, Joachim ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Amino acids; Amino alcohols; Diazo compounds; Lactams; Peptidomimetics

Indexed keywords

3 (1 BENZYLOXYCARBONYLAMINO 2 METHYLPROPYL) 4 (4 CHLOROPHENYL) 1 (4 METHOXYBENZYL)AZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINO 2 METHYLPROPYL) 4 (4 CHLOROPHENYL)AZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINO 2 PHENYLETHYL) 1 (4 METHOXYBENZYL) 4 PHENYL AZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINO 2 PHENYLETHYL) 4 (4 CHLOROPHENYL) 1 (4 METHOXYBENZYL)AZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINO 2 PHENYLETHYL) 4 (4 CHLOROPHENYL)AZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINO 2 PHENYLETHYL) 4 PHENYLAZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINOETHYL) 1 (4 METHOXYBENZYL) 2 OXO AZETIDINE 4 CARBALDEHYDE; 3 (1 BENZYLOXYCARBONYLAMINOETHYL) 1 (4 METHOXYBENZYL) 4 (2 PHENYLETHENYL)AZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINOETHYL) 1 (4 METHOXYBENZYL) 4 PHENYLAZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINOETHYL) 4 (4 CHLOROPHENYL) 1 (4 METHOXYBENZYL)AZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINOETHYL) 4 (4 CHLOROPHENYL)AZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINOETHYL) 4 [1,3]DIOXOLAN 2 YLAZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINOETHYL) 4 PHENYLAZETIDIN 2 ONE; 3 (1 BENZYLOXYCARBONYLAMINOETHYL) 4[1,3]DIOXOLAN 2 YL 1 (4 METHOXYBENZYL)AZETIDIN 2 ONE; ALCOHOL DERIVATIVE; AMINO ACID DERIVATIVE; AZETIDINE DERIVATIVE; BETA LACTAM DERIVATIVE; ESTER DERIVATIVE; GLYCINE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; METHYL 2 (AMINOPHENYLMETHYL) 3 BENZYLOXYCARBONYLAMINOBUTANOIC ACID; METHYL 2 [AMINO (4 CHLOROPHENYL)METHYL] 3 (BENZYLOXYCARBONYLAMINO) 4 PHENYLBUTANOIC ACID; METHYL 2 [AMINO (4 CHLOROPHENYL)METHYL] 3 BENZYLOXYCARBONYLAMINO 4 METHYLPENTANOIC ACID; METHYL 3 BENZYLOXYCARBONYLAMINO 2 (TERT BUTYLOXYCARBONYLAMINO[1,3]DIOXOLAN 2 YL METHYL)BUTANOIC ACID; METHYL 3 BENZYLOXYCARBONYLAMINO 2 (TERT BUTYLOXYCARBONYLAMINOPHENYLMETHYL)BUTANOIC ACID; METHYL 3 BENZYLOXYCARBONYLAMINO 2 [TERT BUTYLOXYCARBONYLAMINO(4 CHLOROPHENYLMETHYL)METHYL]BUTANOIC ACID; SODIUM AZIDE; UNINDEXED DRUG; UREA DERIVATIVE;

ARTICLE; CATALYSIS; CURTIUS REARRANGEMENT; DERIVATIZATION; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; QUANTUM YIELD; REDUCTION; RING OPENING; STEREOCHEMISTRY;

EID: 48049090742     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.006     Document Type: Article

References (59)

1. Hubschwerlen C. In: Taylor J.B., and Triggle D.J. (Eds). Comprehensive Medicinal Chemistry II Vol. 7 (2006), Elsevier, Oxford, UK 479-518
2. Graf R., Lohaus G., Börner K., Schmidt E., and Bestian H. Angew. Chem. 74 (1962) 523-530
3. Angew. Chem., Int. Ed. Engl. 1 (1962) 481-488
4. Bestian H. Angew. Chem. 80 (1968) 304-312
5. Angew. Chem. Int. Ed. Engl. 7 (1968) 278-285
6. Matthews J.L. In: Goodman M., Felix A., Moroder L., and Toniolo C. (Eds). Houben-Weyl, Methods of Organic Chemistry, Synthesis of Peptides and Peptidomimetics Vol. E22c (2003), Georg Thieme, Stuttgart 552-569
7. Seebach D., Beck A.K., and Bierbaum D.J. Chem. Biodivers. 1 (2004) 1111-1239
8. In: Juaristi E., and Soloshonok V.A. (Eds). Enantioselective Synthesis of β-Amino Acids (2005), John Wiley & Sons, Hoboken
9. Holton R.A., Kim H.-B., Somoza C., Liang F., Biediger R.J., Boatman P.D., Shindo M., Smith C.C., Kim S., Nadizadeh H., Suzuki Y., Tao C., Vu P., Tang S., Zhang P., Murthi K.K., Gentile L.N., and Liu J.H. J. Am. Chem. Soc. 116 (1994) 1599-1600
10. Mukerjee A.K., and Singh A.K. Synthesis (1975) 547-589
11. Palomo C., Aizpurua J.M., and Ganboa I. In: Juaristi E. (Ed). Enantioselective Synthesis of β-Amino Acids (1997), Wiley-VCH, New York, NY 279-357
12. Palomo C., Aizpurua J.M., Ganboa I., and Oiarbide M. In: Juaristi E., and Soloshonok V.A. (Eds). Enantioselective Synthesis of β-Amino Acids (2005), Wiley-Interscience, Hoboken, New Jersey, NJ 477-495
13. Alcaide B., Almendros P., and Aragoncillo C. Chem. Rev. 107 (2007) 4437-4492
14. Georg G.I., and Ravikumar V.T. In: Georg G.I. (Ed). The Organic Chemistry of β-Lactams (1993), VCH, New York, NY 295-368
15. Wang Y., Liang Y., Jiao L., Du D.-M., and Xu J. J. Org. Chem. 71 (2006) 6983-6990
16. Podlech J. Synlett (1996) 582-584
17. Podlech J., and Linder M.R. J. Org. Chem. 62 (1997) 5873-5883
18. Podlech J., and Steurer S. Synthesis (1999) 650-654
19. Linder M.R., and Podlech J. Org. Lett. 1 (1999) 869-871
20. Podlech J., Linder M.R., and Maier T.C. In: Attanasi O.A., and Spinelli D. (Eds). Targets in Heterocyclic Systems-Chemistry and Properties Vol. 4 (2000), Società Chimica Italiana, Rom 269-291
21. Linder M.R., Frey W.U., and Podlech J. J. Chem. Soc., Perkin Trans. 1 (2001) 2566-2577
22. Linder M.R., and Podlech J. Org. Lett. 3 (2001) 1849-1851
23. Taubinger A.A., Fenske D., and Podlech J. Synlett (2008) 539-542
24. Ivanov C., and Dryanska V. Dokl. Bulg. Akad. Nauk. 22 (1969) 423-426
25. Chem. Abstr. 71 (1969) 123860
26. Chauveau A., Martens T., Bonin M., Micouin L., and Husson H.-P. Synthesis (2002) 1885-1890
27. Ager D.J. In: Ager D. (Ed). Handbook of Chiral Chemicals (2006), CRC LLC, Boca Raton 11-30
28. e. g. Adams H., Bradshaw D., and Fenton D.E. J. Chem. Soc., Dalton Trans. (2002) 925-930
29. Ng, J. S.; Przybyla, C. A.; Mueller, R. A.; Vasquez, M. L.; Getman, D. P.; Freskos, J. J.; Decrescenzo, G. A.; Bertenshaw, D. E.; Heintz, R. M.; Zhang, S.; Liu, C.; Laneman S. A. (G. D. Searle and Co., USA), WO 9514653, 1995;
30. Chem. Abstr. 123 (1995) 339376
31. Herold, P.; Mah, R.; Stutz, S.; Tschinke, V.; Stojanovic, A.; Marti, C.; Behnke, D.; Jotterand, N.; Quirmbach, M.; Schumacher, C. (Speedel Experimenta AG, Switzerland), EP 1764099, 2007;
32. Chem. Abstr. 146 (2007) 330872
33. Ojima I. In: Georg G.I. (Ed). The Organic Chemistry of β-Lactams (1993), VCH, New York, NY 197-255
34. Shiozaki M., Ishida N., Hiraoka T., and Maruyama H. Tetrahedron 40 (1984) 1795-1802
35. Ojima I., Habus I., Zhao M., Zucco M., Park Y.H., Sun C.M., and Brigaud T. Tetrahedron 48 (1992) 6985-7012
36. Bell M.R., Clemans S.D., and Oesterlin R. J. Med. Chem. 13 (1970) 389-394
37. Podlech J., Gurrath M., Müller G., and Lohof E. In: Goodman M., Felix A., Moroder L., and Toniolo C. (Eds). Houben-Weyl, Methods of Organic Chemistry, Synthesis of Peptides and Peptidomimetics Vol. E22a (2002), Georg Thieme, Stuttgart 41-165
38. Palomo C., Aizpurua J.M., Urchegui R., and Iturburu M. J. Org. Chem. 57 (1992) 1571-1579
39. 10 These and the data for the structure of 53 (CCDC 682044) can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
40. Palomo C., Aizpurua J.M., and Cuevas C. J. Chem. Soc., Chem. Commun. (1994) 1957-1958
41. Palomo C., Aizpurua J.M., Cuevas C., Mielgo A., and Galarza R. Tetrahedron Lett. 36 (1995) 9027-9030
42. Baldwin J.E., Adlington R.M., Gollins D.W., and Schofield C.J. J. Chem. Soc., Chem. Commun. (1990) 720-721
43. Nahm S., and Weinreb S.M. Tetrahedron Lett. 22 (1981) 3815-3818
44. Baldwin J.E., Adlington R.M., Gollins D.W., and Schofield C.J. Tetrahedron 46 (1990) 4733-4748
45. Wilson M.E., and Nowick J.S. In: Goodman M., Felix A., Moroder L., and Toniolo C. (Eds). Houben-Weyl, Methods of Organic Chemistry, Synthesis of Peptides and Peptidomimetics Vol. E22c (2003), Georg Thieme, Stuttgart 590-605
46. Nowick J.S. Acc. Chem. Res. 32 (1999) 287-296
47. Lam P.Y.S., Jadhav P.K., Eyermann C.J., Hodge C.N., Ru Y., Bacheler L.T., Meek J.L., Otto M.J., Rayner M.M., Wong Y.N., Chang C.-H., Weber P.C., Jackson D.A., Sharpe T.R., and Erickson-Viitanen S. Science 263 (1994) 380-384
48. Speeter M.E., and Maroney W.H. J. Am. Chem. Soc. 76 (1954) 5810-5811
49. Testa E., Fontanella L., and Cristiani G.F. Liebigs Ann. Chem. 626 (1959) 114-120
50. Metzger C. Chem. Ber. 104 (1971) 59-64
51. Bose A.K., Banik B.K., Mathur C., Wagle D.R., and Manhas M.S. Tetrahedron 56 (2000) 5603-5619
52. Del Buttero P., Molteni G., and Roncoroni M. Tetrahedron Lett. 47 (2006) 2209-2211
53. Alcaide B., Almendros P., Cabrero G., and Ruiz M.P. J. Org. Chem. 72 (2007) 7980-7991
54. Amundsen L.H., and Nelson L.S. J. Am. Chem. Soc. 73 (1951) 242-244
55. Podlech J., and Seebach D. Liebigs Ann. (1995) 1217-1228
56. Podlech J., and Seebach D. Helv. Chim. Acta 78 (1995) 1238-1246
57. Anderson J.C., Blake A.J., Howell G.P., and Wilson C. J. Org. Chem. 70 (2005) 549-555
58. Still W.C., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923-2925
59. Texier-Boullet F. Synthesis (1985) 679-681