Observations on the synthesis of functionalised methyleneaziridines

Tetrahedron

Volumn 52, Issue 20, 1996, Pages 7037-7044

  Ince, Julie ^a   Ross, Tracey M ^a   Shipman, Michael ^a   Slawin, Alexandra M Z ^a   Ennis, David S ^b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029932369     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00308-0     Document Type: Article

References (18)

1. Pollard, C.B.; Parcell, R.F. J. Am. Chem. Soc. 1951, 73, 2925.
2. Bottini, A.T.; Roberts, J.D. J. Am. Chem. Soc. 1957, 79, 1462.
3. Wijnberg, J.B.P.A.; Wiering, P.G.; Steinberg, H. Synthesis 1981, 901.
4. For an alternative if impractical approach to methyleneaziridines based upon the aziridination of allenes with a nitrene, see Bingham, E.M.; Gilbert, C.J. J. Org. Chem. 1975, 40, 224.
5. Alper, H.; Hamel, N. Tetrahedron Lett. 1987, 28, 3237.
6. For some other chemical reactions of methyleneaziridines, see Cookson, R.C.; Halton, B.; Stevens, I.D.R.; Watts, C.T.J. Chem. Soc. (C) 1967, 928; Quast, H.; Risler, W. Ang. Chem. Int. Ed. Engl. 1973, 12, 414; Crandall, J.K.; Crawley, L.C.; Kobin, J.B. J. Org. Chem. 1975, 40, 2045.; Quast, H.; Vélez, C.A.W. Ang. Chem. Int. Ed. Engl. 1978, 17, 213; Jongejan, E.; Steinberg, H.; de Boer, T.J. Recl. Trav. Chim. Pays-Bas 1979, 98, 66; Alasaka, T.; Nomura, Y.; Ando, W. J. Org. Chem. 1988, 53, 1670.
7. For some other chemical reactions of methyleneaziridines, see Cookson, R.C.; Halton, B.; Stevens, I.D.R.; Watts, C.T.J. Chem. Soc. (C) 1967, 928; Quast, H.; Risler, W. Ang. Chem. Int. Ed. Engl. 1973, 12, 414; Crandall, J.K.; Crawley, L.C.; Kobin, J.B. J. Org. Chem. 1975, 40, 2045.; Quast, H.; Vélez, C.A.W. Ang. Chem. Int. Ed. Engl. 1978, 17, 213; Jongejan, E.; Steinberg, H.; de Boer, T.J. Recl. Trav. Chim. Pays-Bas 1979, 98, 66; Alasaka, T.; Nomura, Y.; Ando, W. J. Org. Chem. 1988, 53, 1670.
8. For some other chemical reactions of methyleneaziridines, see Cookson, R.C.; Halton, B.; Stevens, I.D.R.; Watts, C.T.J. Chem. Soc. (C) 1967, 928; Quast, H.; Risler, W. Ang. Chem. Int. Ed. Engl. 1973, 12, 414; Crandall, J.K.; Crawley, L.C.; Kobin, J.B. J. Org. Chem. 1975, 40, 2045.; Quast, H.; Vélez, C.A.W. Ang. Chem. Int. Ed. Engl. 1978, 17, 213; Jongejan, E.; Steinberg, H.; de Boer, T.J. Recl. Trav. Chim. Pays-Bas 1979, 98, 66; Alasaka, T.; Nomura, Y.; Ando, W. J. Org. Chem. 1988, 53, 1670.
9. For some other chemical reactions of methyleneaziridines, see Cookson, R.C.; Halton, B.; Stevens, I.D.R.; Watts, C.T.J. Chem. Soc. (C) 1967, 928; Quast, H.; Risler, W. Ang. Chem. Int. Ed. Engl. 1973, 12, 414; Crandall, J.K.; Crawley, L.C.; Kobin, J.B. J. Org. Chem. 1975, 40, 2045.; Quast, H.; Vélez, C.A.W. Ang. Chem. Int. Ed. Engl. 1978, 17, 213; Jongejan, E.; Steinberg, H.; de Boer, T.J. Recl. Trav. Chim. Pays-Bas 1979, 98, 66; Alasaka, T.; Nomura, Y.; Ando, W. J. Org. Chem. 1988, 53, 1670.
10. For some other chemical reactions of methyleneaziridines, see Cookson, R.C.; Halton, B.; Stevens, I.D.R.; Watts, C.T.J. Chem. Soc. (C) 1967, 928; Quast, H.; Risler, W. Ang. Chem. Int. Ed. Engl. 1973, 12, 414; Crandall, J.K.; Crawley, L.C.; Kobin, J.B. J. Org. Chem. 1975, 40, 2045.; Quast, H.; Vélez, C.A.W. Ang. Chem. Int. Ed. Engl. 1978, 17, 213; Jongejan, E.; Steinberg, H.; de Boer, T.J. Recl. Trav. Chim. Pays-Bas 1979, 98, 66; Alasaka, T.; Nomura, Y.; Ando, W. J. Org. Chem. 1988, 53, 1670.
11. For some other chemical reactions of methyleneaziridines, see Cookson, R.C.; Halton, B.; Stevens, I.D.R.; Watts, C.T.J. Chem. Soc. (C) 1967, 928; Quast, H.; Risler, W. Ang. Chem. Int. Ed. Engl. 1973, 12, 414; Crandall, J.K.; Crawley, L.C.; Kobin, J.B. J. Org. Chem. 1975, 40, 2045.; Quast, H.; Vélez, C.A.W. Ang. Chem. Int. Ed. Engl. 1978, 17, 213; Jongejan, E.; Steinberg, H.; de Boer, T.J. Recl. Trav. Chim. Pays-Bas 1979, 98, 66; Alasaka, T.; Nomura, Y.; Ando, W. J. Org. Chem. 1988, 53, 1670.
12. Perhaps the most complex methyleneaziridine prepared to date is 1-(2-methylene-1-aziridyl)-3-buten-2-o1 prepared by Bottini, A.T.; Dev, V. J. Org. Chem., 1962, 27, 968.
13. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis, Wiley, New York, 1991.
14. Bottini, A.T.; Dev, V.; Klinck, J. Organic Syntheses: Collective Volume V, pp121-124.
15. Quast, H.; Jakob, R.; Peters, K.; Peters, E.-M.; von Schnering, H.G. Chem. Ber. 1984, 117, 840.
16. The refined atomic coordinates for this structure have been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
17. Bottini, A.T.; Olsen, R.E. J. Am. Chem. Soc. 1962, 84, 195.
18. Casara, P.; Danzin, C.; Metcalf B.; Jung, M. J. Chem. Soc., Perkin Trans. 1, 1985, 2201.