Diversion from Bicyclo[4.2.0]octanol Formation Through the Use of Vinyl Electrophiles

Abstract

Bicyclo[4.2.0]octanols can be obtained from the reaction of phenyl vinyl sulfoxide and the lithium enolate of cyclohexanone under controlled conditions. Diversion to alkylation or Michael-Michael-ring closure was observed when alternative vinyl electrophiles were used. Novel bicyclic disulfones and hydroxyhexahydronaphthalenes were isolated. The use of a vinyl sulfoxide electrophile is crucial to the formation of bicyclo[4.2.0]octanols from simple ketones.

Key words

alkylations - bicyclic compounds - ketones - Michael additions - ring closure

References

• 1 Loughlin WA. Rowen CC. Healy PC. J. Chem. Soc., Perkin Trans. 2  2002,  296 
• 2 Loughlin WA. Rowen CC. Healy PC. J. Org. Chem.  2004,  69:  5690 
• 3 Loughlin WA. McCleary MA. Org. Biomol. Chem.  2003,  1:  1347 
• 4 Loughlin WA. McCleary MA. Synthesis  2005,  761 
• 5 Cabiddu MG. Cabiddu S. Cadoni E. Cannas R. Fattuoni C. Melis S. Tetrahedron  1998,  54:  14095 
• 6 Bunlaksananusorn T. Rodriguez AL. Knochel P. Chem. Commun.  2001,  745 
• 7 Risaliti A. Fatutta S. Forchiassin M. Tetrahedron  1967,  23:  1451 
• 8 Fatutta S. Risaliti A. J. Chem. Soc., Perkin Trans. 1  1974,  2387 
• 10a Pearson AJ. Mortezaei R. Tetrahedron Lett.  1989,  30:  5049 
• 10b Auvray P. Knochel P. Normant JF. Tetrahedron  1988,  44:  6095 
• 11a Cory RM. Renneboog RM. J. Org. Chem.  1984,  49:  3898 
• 11b Cory RM. Renneboog RM. J. Chem. Soc., Chem. Commun.  1980,  1081 
• 12 Hagiwara H. Endou S. Fukushima M. Hoshi T. Suzuki T. Org. Lett.  2004,  6:  1115 
• 13 Hagiwara H. Akama T. Okano A. Uda H. J. Chem. Soc., Perkin Trans. 1  1993,  2173 
• 14 Haynes RK. Loughlin WA. Hambley TW. J. Org. Chem.  1991,  56:  5785 
• 15a Ye B. Qiao L.-X. Zhang Y.-B. Wu Y.-L. Tetrahedron  1994,  50:  9061 
• 15b Posner GH. Lu S.-B. Asirvatham E. Silversmith EF. Shulman EM. J. Am. Chem. Soc.  1986,  108:  511 
• 15c Posner GH. Asirvatham E. Tetrahedron Lett.  1986,  27:  663 
• 15d Dionne G. Engel CR. Can. J. Chem.  1978,  56:  419 
• 16 Collins DJ. Rowley LE. Swan JM. Aust. J. Chem.  1974,  27:  841 
• 17 Wallace P. Warren S. J. Chem. Soc., Perkin Trans. 1  1992,  3169 
• 18 TeXsan for Windows Version 1.06, 2001   Molecular Structure Corporation; The Woodlands, TX: 2001. 
• 19 Sheldrick GM. SHELX-97 Program for Crystal Structure Determination   University of Göttingen; Göttingen: 1997. 
• 20 Farrugia LJ. J. Appl. Cryst.  1997,  30:  565 

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Atom coordinates, bond lengths, angles and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre for structures 9-12 (CCDC reference numbers 265361-265364, respectively). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax:+ 44 (1223)336033; email:[e-mail]).