A convenient synthesis of N-boc-protected α-aminonitriles from α-amidosulfones

Synthetic Communications

Volumn 34, Issue 17, 2004, Pages 3147-3160

  Banphavichit, Vorawit ^a   Chaleawlertumpon, Saowaluk ^a   Bhanthumnavin, Worawan ^a   Vilaivan, Tirayut ^a  

^a CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Amino acids; Imines; Nucleophilic additions; Phase transfer catalysis; Strecker

Indexed keywords

N TERT BUTYLOXYCARBONYL 2 AMINO 3 METHYL BUTYRONITRILE; N TERT BUTYLOXYCARBONYL 2 AMINO 3 PHENYL PROPIONITRILE; N TERT BUTYLOXYCARBONYL 2 AMINO 3,3 DIMETHYL BUTYRONITRILE; N TERT BUTYLOXYCARBONYL 2 AMINO 4 METHYL VALERONITRILE; N TERT BUTYLOXYCARBONYL 2 AMINO 4 PHENYL BUTYRONITRILE; N TERT BUTYLOXYCARBONYL 2 AMINOBUTYRONITRILE; N TERT BUTYLOXYCARBONYL 2 AMINOCYCLOHEXYLACETONITRILE; N TERT BUTYLOXYCARBONYL 2 AMINOHEXANENITRILE; N TERT BUTYLOXYCARBONYL 2 AMINOUNDECANENITRILE; N TERT BUTYLOXYCARBONYL 2 AMINOVALERONITRILE; N TERT BUTYLOXYCARBONYLAMINO (1 NAPHTHYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (2 FURYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (2 THIENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (2' METHOXYPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (2' NITROPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (3' HYDROXYPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (3' METHOXYPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (3' NITROPHENYL) ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (4' BROMOPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (4' CHLOROPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (4' CYANOPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (4' FLUOROPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (4' ISOPROPYLPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (4' METHOXYPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (4' METHYLPHENYL)ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (4' NITROPHENYL) ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO (4' TERT BUTYLPHENYL) ACETONITRILE; N TERT BUTYLOXYCARBONYLAMINO PHENYLACETONITRILE; NITRILE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; HYDROLYSIS; SYNTHESIS;

EID: 5344262439     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200028592     Document Type: Article

References (36)

1. (a) Eliel, E.L.; Freeman, J.P. Atrolactic acid. In Organic Syntheses; Coll. Vol. 4, 58;
2. (b) Kendall, E.C.; McKenzie, B.F. DL-Alanine. In Organic Syntheses; Coll. Vol. 1, 21;
3. (c) Steiger, R.E. DL-α-aminophenylacetic acid* (glycine, α-phenyl-). In Organic Syntheses; Coll. Vol. 3, 84;
4. (d) Deng, S.-L.; Liu, D.-Z. Studies on phosphoroheterocycle chemistry II: a simple and new route to 1,3,2-diazaphospholidine-4-thione 2-sulfide derivatives. Synthesis 2001, 2445-2449.
5. Mowry, D.T. The preparation of nitriles. Chem. Rev. 1948, 42, 189-283.
6. (a) McLaughlin, M.; Mohareb, R.M.; Rapoport, H. An efficient procedure for the preparation of 4-substituted 5-aminoimidazoles. J. Org. Chem. 2003, 68, 50-54;
7. (b) Demko, Z.P.; Sharpless, K.B. An expedient route to the tetrazole analogues of α-amino acids. Org. Lett. 2002, 4, 2525-2527;
8. (c) Zhong, Y.L.; Lee, J.; Reamer, R.A.; Askin, D. New method for the synthesis of diversely functionalized imidazoles from N-acylated-aminonitriles. Org. Lett. 2004, 6, 929-931.
9. (a) Bailly, C.; Houssin, R.; Bernier, J.-L.; Henichart, J.-P. Depsipeptide analogs of the antitumor drug distamycin containing thiazole amino acids residues. Tetrahedron 1988, 44, 5833-5844;
10. (b) Umemura, K.; Tate, T.; Yamaura, M.; Yoshimura, J.; Yonezawa, Y.; Shin, C.-G. A facile synthesis of fragment-D of antibiotic, nosiheptide. Synthesis 1995, 1423-1426;
11. (c) Costello, G.F.; James, R.; Shaw, J.S.; Slater, A.M.; Stutchbury, N.C.J. 2-(3,4-Dichlorophenyl)-N-methyl-N-[2-(1-pyrrolidinyl)-1-substituted- ethyl]-acetamides: the use of conformational analysis in the development of a novel series of potent opioid kappa agonists. J. Med. Chem. 1991, 34, 181-189;
12. (d) Greenspan, P.D.; Clark, K.L.; Tommasi, R.A.; Cowen, S.D.; McQuire, L.W.; Farley, D.L.; van Duzer, J.H.; Goldberg, R.L.; Zhou, H.; Du, Z.; Fitt, J.J.; Coppa, D.E.; Fang, Z.; Macchia, W.; Zhu, L.; Capparelli, M.P.; Goldstein, R.; Wigg, A.M.; Doughty, J.R.; Bohacek, R.S.; Knapet, A.K. Identification of dipeptidyl nitriles as potent and selective inhibitors of cathepsin B through structure-based drug design. J. Med. Chem. 2001, 44, 4524-4534.
13. (a) Boeijen, A.; Liskamp, R.M.J. Solid-phase synthesis of oligourea peptidomimetics. Eur. J. Org. Chem. 1999, 2127-2135;
14. (b) Hone, N.D.; Payne, L.J.; Tice, C.M. Direct release of nitriles from solid phase. Tetrahedron Lett. 2001, 42, 1115-1118;
15. (c) Thompson, S.A.; Andrews, P.R.; Hanzlik, R.P. Carboxyl-modified amino acids and peptides as protease inhibitors. J. Med. Chem. 1986, 29, 104-111.
16. Maetz, P.; Rodriguez, M. A simple preparation of N-protected chiral α-aminonitriles from N-protected α-amino acid amides. Tetrahedron Lett. 1997, 38, 4221-4222.
17. Nakajima, N.; Saito, M.; Ubukata, M. Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates. Tetrahedron 2002, 58, 3561-3578.
18. Bose, D.S.; Jayalakshmi, B. Reagents for organic synthesis: use of organostannyl oxides as catalytic neutral agents in the preparation of nitriles from primary amides under microwave irradiation. J. Org. Chem. 1999, 64, 1713-1714.
19. (a) Katritzky, A.R.; Urogdi, L. Benzotriazole-assisted synthesis of α-acyl-aminonitriles and a conceptually novel methods for peptide elongation. J. Chem. Soc. Perkin Trans. 1 1990, 1853-1857;
20. (b) Katritzky, A.R.; Shobana, N.; Harris, P.A. A new synthesis of an amino acid based sweetener. Org. Prep. Proc. Int. 1992, 24, 121-126.
21. Pearson, W.H.; Lindbeck, A.C.; Kampf, J.W. Configurational stability of chiral, nonconjugated nitrogen-substituted organolithium compounds generated by tin-lithium exchange of N-[(1-tri-n-butylstannyl)alkyl]imidazolidin-2-ones and -oxazolidin-2-ones. J. Am. Chem. Soc. 1993, 115, 2622-2636.
22. Engberts, J.B.F.N.; Strating, J. The Mannich condensation of sulfinic acids, aldehyde, and ethyl carbamate. II. The use of higher aldehydes. Recl. Trav. Chim. Pays-Bas 1965, 84, 942-950.
23. Kanazawa, A.M.; Denis, J.-N.; Greene, A.E. Highly stereocontrolled and efficient preparation of the protected, esterification-ready docetaxel (Taxotere) side chain. J. Org. Chem. 1994, 59, 1238-1240.
24. Mecozzi, T.; Petrini, M.; Profeta, R. Reaction of α- amidoalkylphenyl sulfones with lithiated nitriles: syn-selective synthesis of β-amino nitriles. J. Org. Chem. 2001, 66, 8264-8267.
25. Mecozzi, T.; Petrini, M. Synthesis of allylic and propargylic primary amines by reaction of organometallic reagents with α-amidoalkyl sulfones. J. Org. Chem. 1999, 64, 8970-8972.
26. Mecozzi, T.; Petrini, M. Reaction of α-amidoalkylphenyl sulfones with Reformatsky reagents. A new entry to α-amino esters. Tetrahedron Lett. 2000, 41, 2709-2712.
27. Petrini, M.; Profeta, R.; Righi, P. Reaction of allylzinc reagents and zinc enolates of ketones with α-amidoalkylphenyl sulfones. J. Org. Chem. 2002, 67, 4530-4535.
28. Dahmen, S.; Braese, S. The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands. J. Am. Chem. Soc. 2002, 124, 5940-5941.
29. Murry, J.A.; Frantz, D.E.; Soheili, A.; Tillyer, R.; Grabowski, E.J.J.; Reider, P.J. Synthesis of α-amido ketones via organic catalysis: thiazolium-catalyzed cross-coupling of aldehydes with acylimines. J. Am. Chem. Soc. 2001, 123, 9696-9697.
30. Bernacka, E.; Klepacs, A.; Zwierzak, A. Reductive Boc-amination of aldehydes. Tetrahedron Lett. 2001, 42, 5093-5094.
31. Klepacz, A.; Zwierzak, A. An expeditious one-pot synthesis of diethyl N-boc-1-aminoalkylphosphonates. Tetrahedron Lett. 2002, 43, 1079-1080.
32. Zhang, J.; Wei, C.; Li, C.-J. Cu(I)Br mediated coupling of alkynes with N-acylimine and N-acyliminium ions in water. Tetrahedron Lett. 2002, 43, 5731-5733.
33. Ballini, R.; Petrini, M. Base assisted substitution of α-amidoalkyl sulfones by nitromethane anion. A new entry to functionalized α-amino acids. Tetrahedron Lett. 1999, 40, 4449-4452.
34. (a) Jaafar, I.; Francis, G.; Danion-Bougot, R.; Danion, D. α-Isocyanato-acrylonitriles from alkylidenecyanoacetic or arylidenecyanoacetic acids - synthesis and reactions. Synthesis 1994, 56-60;
35. (b) Cativiela, C.; Diaz-de-Villegas, M.D.; Galvez, J.A.; Lapena, Y. On the synthesis of (S)-α-methylaspartic acid by diastereoselective alkylation of a chiral 2-cyanopropanoate. Tetrahedron 1997, 53, 5891-5898;
36. (c) Decicco, C.P.; Grover, P. Asymmetric amino acid synthesis: Mitsunobu reactions on chiral cyanohydrins. Synlett 1997, 529-530.