The [3 + 2] annulation of allylsilanes and chlorosulfonyl isocyanate: Stereoselective synthesis of 2-pyrrolidinones

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1434-1435

  Roberson, Claudia W ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033525840     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982375x     Document Type: Article

References (27)

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11. The details are provided as Supporting Information.
12. 4 and concentrated in vacuo. Purification by flash chromatography (3:1 hexanes:EtOAc) provided 3c as an oil that solidified on standing (0.166 g, 75%). Spectral and analytical data confirmed the structure of the product.
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15. 3). (matrix presented)
16. Enantiopure (E)-crotylsilanes have been used in [3 + 2] annulations. See, for example: Panek, J. S.; Jain, N. F. J. Org. Chem. 1993, 58, 2345-2348.
17. For a recent example of a [2 + 2] annulation of an allylsilane, see: Knölker, H.-J.; Baum, E.; Schmitt, O. Tetrahedron Lett. 1998, 39, 7705-7708.
18. Allylsilane 4b has been shown to undergo [3 + 2] annulation reactions with enones: (a) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R.; Jones, P. G.; Wanzl, G. Chem. Eur. J. 1997, 3, 538-550.
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22. Siliranium ions have also been proposed as intermediates in annulation reactions: Knölker, H.-J.; Foitzik, N.; Graf, R.; Pannek, J.-B.; Jones, P. G. Tetrahedron 1993, 49, 9955-9972.
23. Seyferth, D.; White, D. L. J. Am. Chem. Soc. 1972, 94, 3132-3138.
24. The importance of allylic substitution to annulation yield has been observed by other researchers: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R W. J. Org. Chem. 1992, 57, 6094-6097.
25. (b) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627-630.
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27. For an excellent discussion of the structure and stability of β-silyl carbocations, see: Lambert, J. B. Tetrahedron 1990, 46, 2677-2689.