The generation and cycloaddition of 2-azaallyl anions and azomethine ylides from a common precursor. A novel synthesis of indolizidines and other heterocycles

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5441-5444

  Pearson, William H ^a   Mi, Yuan ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; INDOLIZIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030872615     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01217-3     Document Type: Article

References (28)

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11. (c) Vedejs, E. In Advances in Cycloaddition; D. P. Curran, Ed.; JAI Press: Greenwich, CT, 1988; Vol. 1; pp 33-51.
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15. Tin-lithium exchange is extremely fast, thus the n-butyllithium should not react at the leaving group X. The cyclization of 6 by displacement of X by a carbanionic site was of some concern, but since the C-alkylation of organolithiums by organic halides is not an efficient reaction, we felt that cycloaddition might compete effectively, especially if a good anionophile were already present.
16. The intramolecular N-alkylation of imines is a popular method for the formation of nitrogen heterocycles. For example, see: (a) Evans, D. A. J. Am. Chem. Soc. 1970, 92, 7593-7595.
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18. (c) Stevens, C.; De Kimpe, N. SYNLETT 1991, 351-352.
19. Azomethine ylide cycloadditions have been used to prepare pyrrolizidines and indolizidines. See references 2c-2e, 7, and Pandey, G.; Lakshmaiah, G. Tetrahedron Lett. 1993, 34, 4861-4864.
20. (a) Vedejs, E.; Martinez, G. R. J. Am. Chem. Soc. 1979, 101, 6452-6454.
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22. Terao, Y.; Aono, M.; Achiwa, K. Heterocycles 1988, 27, 981-1008.
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25. 3 (Letellier, M.; McPhee, D. J.; Griller, D. Synth. Commun. 1988, 18, 1975-1978.). This technique for making such ω-haloimines was reported by Kuehne; see: Kuehne, M. E.; Matsko, T. H.; Bohnert, J. C.; Motyka, L.; Oliver-Smith, D. J. Org. Chem 1981, 46, 2002-2009. For closely related work, see also De Kimpe in reference 4c above. Similar strategies were used to make imines 14 and 18.
26. 3 (Letellier, M.; McPhee, D. J.; Griller, D. Synth. Commun. 1988, 18, 1975-1978.). This technique for making such ω-haloimines was reported by Kuehne; see: Kuehne, M. E.; Matsko, T. H.; Bohnert, J. C.; Motyka, L.; Oliver-Smith, D. J. Org. Chem 1981, 46, 2002-2009. For closely related work, see also De Kimpe in reference 4c above. Similar strategies were used to make imines 14 and 18.
27. Chong, J. M.; Park, S. B. J. Org. Chem 1992, 57, 2220-2222.
28. Preparation of 5-bromopentanal: Kulkarni, S. U.; Patil, V. D. Heterocycles 1982, 18, 163-167.