Cyclopentene Synthesis from 1,3-dienes via base-induced ring contraction of 3,6-dihydro-2H-thiopyrans: Studies on diastereoselection and mechanism

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4725-4738

  Larsen, Scott D ^a   Fisher, Peter V ^a   Libby, Brian E ^c   Jensen, Randy M ^a   Mizsak, Stephen A ^a   Watt, William ^a   Ronk, Warren R ^b   Hill, Scott T ^b  

^a PFIZER INC   (United States)

^b ALMA COLLEGE   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037601022     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960537o     Document Type: Article

References (48)

1. Undergraduate research participant from Kalamazoo College, Kalamazoo, MI.
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32. For closely related thioketone generations and [4 + 2] cycloadditions see: (a) Abelman, M. M. Tetrahedron Lett. 1991, 32, 7389. (b) Pinto, I. L.; Buckle, D. R.; Rami, H. K.; Smith, D. G. Tetrahedron Lett. 1992, 33, 7597. (c) Capozzi, G.; Menichetti, S.; Nativi, C.; Rosi, A. Tetrahedron 1992, 48, 9023.
33. For closely related thioketone generations and [4 + 2] cycloadditions see: (a) Abelman, M. M. Tetrahedron Lett. 1991, 32, 7389. (b) Pinto, I. L.; Buckle, D. R.; Rami, H. K.; Smith, D. G. Tetrahedron Lett. 1992, 33, 7597. (c) Capozzi, G.; Menichetti, S.; Nativi, C.; Rosi, A. Tetrahedron 1992, 48, 9023.
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36. HMPA is now considered to be a highly dangerous carcinogen! We have recently observed that N,N′-dimethyl-N,N′-propyleneurea (DMPU) may be substituted for HMPA in several of the reactions described herein with little or no loss of stereoselectivity. Mukhopadhyay, T.; Seebach, D. Helv. Chin. Acta 1982, 65, 385.
37. ORTEP diagrams for structures 12j, 12m, and 21 and NOE analyses of structures 11a, 11d, 12d, 12f, 13b, 13c, 14b, 14c, 18m, 19, and 20 are provided in the supporting information. The full X-ray data will also be included in a separate manuscript: Watt, W.; Fisher, P. V.; Larsen, S. D. Acta Cryst. Sect. B 1996, submitted for publication. The author has deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
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39. Regioisomer assignments for the mixture of isomers were made based on NOE analysis (see supporting information). Diastereomer assignments were made based on the relative chemical shifts of the C-2 methine protons (vide supra).
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