Highly stereoselective formal [3 + 3] cycloaddition reactions of chiral vinylogous amides with α,β-unsaturated iminiums

Organic Letters

Volumn 2, Issue 8, 2000, Pages 1161-1164

  Sklenicka, Heather M ^a   Hsung, Richard P ^a   Wei, Lin Li ^a   McLaughlin, Michael J ^a   Gerasyuto, Aleksey I ^a   Degen, Shane J ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000193493     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000049+     Document Type: Article

References (28)

1. UMN Undergraduate Research Participants: 1998-1999. Recipients of 1998 and 1999 LANDO-NSF REU Fellowships.
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5. (b) Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Shen, H. C.; McLaughlin, M. J.; Zehnder, L. R. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Greenwich, CT; in press.
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18. Examples of [3 + 3] cycloaddition reactions in the truest sense are extremely scarce, and there are only limited examples of metal-mediated [3 + 3] cycloaddition reactions. For recent reviews, see: (a) Frühauf, H.-W. Chem. Rev. 1997, 97, 523.
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22. 13C NMR, FTIR, and mass spectroscopy. Details may be obtained from the Supporting Information.
23. For another precedent, see: Moorhoff, C. M. Synthesis 1997, 685.
24. 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.
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