Expeditious synthesis of aziridine-based cofactor mimics

Tetrahedron

Volumn 58, Issue 30, 2002, Pages 6019-6026

  Comstock, Lindsay R ^a   Rajski, Scott R ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

5 aminoadenosine; Aziridine based cofactor mimics; Gabriel Cromwell; S adenosyl L methionine

Indexed keywords

ADENINE; ADENOSINE DERIVATIVE; AZIRIDINE DERIVATIVE; METHYLTRANSFERASE; PROPIONIC ACID DERIVATIVE; S ADENOSYLMETHIONINE;

ALKYLATION; ARTICLE; AZIRIDINATION; CHEMICAL REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0037157806     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00590-2     Document Type: Article

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42. For examples of Gabriel-Cromwell aziridinations see: (a) DeShong P., Kell D.A., Sidler D.R. J. Org. Chem. 50:1985;2309-2315 (b) Stolberg M.A., O'Neill J.J., Wagner-Jauregg T. J. Am. Chem. Soc. 75:1953;5045-5047 (c) Filigheddu S.N., Taddei M. Tetrahedron Lett. 39:1998;3857-3860 (d) Eastwood F.W., Perimutter P., Yang Q. Tetrahedron Lett. 35:1994;2039-2042 (e) Saint-Fuscien C., Tarrade A., Dauben P., Dodd R.H. Tetrahedron Lett. 41:2000;6393-6397.
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44. For asymmetric Gabriel-Cromwell entries see: (a) Cardillo G., Gentilucci L., Tomasini C., Pilar V., Castejon-Bordas M. Tetrahedron: Asymmetry. 7:1996;755-762 (b) Clark W.M., Bender C. J. Org. Chem. 63:1998;6732-6743 (c) Guillena G., Nájera C. J. Org. Chem. 65:2000;7310-7322 (d) Jahnisch K., Tittelbach F., Grundemann E., Schneider M. Eur. J. Org. Chem. 2000;3957-3960.
45. For asymmetric Gabriel-Cromwell entries see: (a) Cardillo G., Gentilucci L., Tomasini C., Pilar V., Castejon-Bordas M. Tetrahedron: Asymmetry. 7:1996;755-762 (b) Clark W.M., Bender C. J. Org. Chem. 63:1998;6732-6743 (c) Guillena G., Nájera C. J. Org. Chem. 65:2000;7310-7322 (d) Jahnisch K., Tittelbach F., Grundemann E., Schneider M. Eur. J. Org. Chem. 2000;3957-3960.
46. For asymmetric Gabriel-Cromwell entries see: (a) Cardillo G., Gentilucci L., Tomasini C., Pilar V., Castejon-Bordas M. Tetrahedron: Asymmetry. 7:1996;755-762 (b) Clark W.M., Bender C. J. Org. Chem. 63:1998;6732-6743 (c) Guillena G., Nájera C. J. Org. Chem. 65:2000;7310-7322 (d) Jahnisch K., Tittelbach F., Grundemann E., Schneider M. Eur. J. Org. Chem. 2000;3957-3960.
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49. For related reductions of aziridines see: (a) Ambrosi, H.-D.; Duczek, W.; Ramm, M.; GrÜndemann, E.; Schulz, B.; Jähnisch, K. Liebigs Ann. Chem. 1994, 1013-1018. (b) Davis, F. A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525-7528. (c) Morimoto, Y.; Matsuda, F.; Shirahama, H. Synlett 1991, 201-203.
50. For related reductions of aziridines see: (a) Ambrosi, H.-D.; Duczek, W.; Ramm, M.; GrÜndemann, E.; Schulz, B.; Jähnisch, K. Liebigs Ann. Chem. 1994, 1013-1018. (b) Davis, F. A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525-7528. (c) Morimoto, Y.; Matsuda, F.; Shirahama, H. Synlett 1991, 201-203.
51. For related reductions of aziridines see: (a) Ambrosi, H.-D.; Duczek, W.; Ramm, M.; GrÜndemann, E.; Schulz, B.; Jähnisch, K. Liebigs Ann. Chem. 1994, 1013-1018. (b) Davis, F. A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525-7528. (c) Morimoto, Y.; Matsuda, F.; Shirahama, H. Synlett 1991, 201-203.
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