Formal cycloaddition reactions of vinylogous amides with α,β-Unsaturated iminiums. A strategy for constructing piperidinyl heterocycles

Organic Letters

Volumn 1, Issue 3, 1999, Pages 509-512

  Hsung, Richard P ^a   Wei, Lin Li ^a   Sklenicka, Heather M ^a   Douglas, Christopher J ^a   McLaughlin, Michael J ^a   Mulder, Jason A ^a   Yao, Letitia J ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000546380     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990107v     Document Type: Article

References (23)

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2. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
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11. (e) Douglas, C. J.; Skelenica, H. M.; Shen, H. C.; Mathias, D. S.; Golding, G. M.; Hsung, R. P.; Degen, S. J.; Morgan, C. D.; Mueller, K. L.; Seurer, L. M.; Shih, R. A. Tetrahedron, submitted for publication.
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14. 13C NMR, FTIR, and mass spectroscopy.
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17. The regiochemical issues were assigned by nOe experiments later on compound 14.
18. We are assuming that the imine nitrogen rather than an iminium species is involved in the ring closure because of the presence of excess piperidine. For a related reference see: Kametani, T.; Kajiwara, M.; Fukumoto, K. Tetrahedron 1974, 30, 1053.
19. For a review see: Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 43, p 185.
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22. 16
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