Triple Mukaiyama-Michael Cascade toward a Tricyclic Framework

Abstract

The intermolecular Mukaiyama-Michael addition between stoichiometric amounts of a bisketene acetal and methyl vinyl ketone is rapidly followed by a double cascade intramolecular Mukaiyama-Michael addition to form a fused tricyclic compound containing four-, five- and six-membered rings embellished with several functionalities.

Key words

Mukaiyama-Michael addition - cascade reaction - fused tricyclic framework - silyl enol ethers - bisketene acetals

References

• 1a Avasthi K. Salomon RG. J. Org. Chem.  1986,  51:  2556 
• 1b Salomon RG. Tetrahedron  1983,  39:  485 
• 2 Ghosh S. Raychaudhuri SR. Salomon RG. J. Org. Chem.  1987,  52:  83 
• 3a Kakiuchi K. Tobe Y. Odaira Y. Bull. Chem. Soc. Jpn.  1982,  55:  921 
• 3b Tobe Y. Kakiuchi K. Kawami Y. Sakai Y. Kimura K. Odaira Y. Chem. Lett.  1978,  1027 
• 3c Tobe Y. Sato J. Sorori T. Kakiuchi K. Odaira Y. Tetrahedron Lett.  1986,  27:  2905 
• 4a Boger DL. Mullican MD. J. Org. Chem.  1984,  49:  4033 
• 4b Markó IE. Evans GR. Seres P. Chellé I. Janousek Z. Pure Appl. Chem.  1996,  68:  113 
• 5 Quendo A. Rousseau G. Synth. Commun.  1989,  19:  1551 
• 6 Nicolaou KC. Jautelat R. Vassilikogiannakis G. Baran PS. Simonsen KB. Chem. Eur. J.  1999,  5:  3651 
• 7 Gennari C. Colombo L. Bertolini G. Schimperana G. J. Org. Chem.  1987,  52:  2754 
• 8 Mukaiyama T. Homma K. Takenoshita H. Chem. Lett.  1989,  1725 
• 9 Faltz H. Bohrisch J. Wohlauf W. Pätzel M. Jones PG. Liebscher J. Tetrahedron  1996,  52:  9035 
• 10 Mayr H. Patz M. Angew. Chem., Int. Ed. Engl.  1994,  33:  938 
• 11 Nonius KappaCCD Server Software   Nonius BV; Delft: 1997. 
• 12 Otwinowski Z. Minor W. Methods Enzymol.  1997,  276:  307 
• 14 Sheldrick GM. SHELXL-97 Program for the Refinement of Crystal Structures   University of Göttingen; Göttingen: 1997. 
• 15 ORTEP, TEXRAY Structure Analysis Package   MSC; The Woodlands (TX, USA): 1999. 

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Mackay, S.; Gilmore, C. J.; Edwards, C.; Tremayne, M.; Stuart, N.; Shankland, K. maXus: A Computer Program for the Solution and Refinement of Crystal Structures from Diffraction Data; University of Glasgow: Glasgow/Nonius BV: Delft/MacScience Co. Ltd.: Yokohama, 1998.

16

Crystallographic data for the structure 6 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 821687. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: [phone]; E-mail: [e-mail].