Allenes as Dipolarophiles in the Intramolecular Carbene Cyclization-Cyclo­addition Cascade Reaction

Abstract

Intramolecular carbene cyclization-cycloaddition cascade reactions with allenes occur efficiently in the presence of dirhodium catalysts to afford oxatricyclic products as single dia­stereomers.

Key words

allenes - carbenoids - cyclization - cycloadditions - domino reactions

References and Notes

• 2a Matsuda H. Morikawa T. Ninomiya K. Yoshikawa M. Tetrahedron  2001,  57:  8443 
• 2b Matsuda H. Ninomiya K. Morikawa T. Yoshikawa M. Bioorg. Med. Chem. Lett.  1998,  8:  339 
• 3a Padwa A. Hornbuckle SF. Chem. Rev.  1991,  91:  263 
• 3b Padwa A. Weingarten MD. Chem. Rev.  1996,  96:  223 
• 3c Padwa A. Chem. Commun.  1998,  1417 
• 3d Doyle MP. McKervey MA. Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds   J. Wiley and Sons; New York: 1998.  Chap. 7. p.397-416  
• 4 Mehta G. Muthusamy S. Tetrahedron  2002,  58:  9477 
• 5a Chiu P. Chen B. Cheng KF. Org. Lett.  2001,  3:  1721 
• 5b Chen B. Ko RYY. Yuen MSM. Cheng KF. Chiu P. J. Org. Chem.  2003,  68:  4195 
• 5c Chiu P. Pure Appl. Chem.  2005,  77:  1183 
• 6 The [3+2] cycloadditions of non-stabilized carbonyl ylides with methoxyallenes has been reported: Hojo M. Aihara H. Hosomi A. J. Am. Chem. Soc.  1996,  118:  3533 
• 7a Ko YY. PhD Dissertation   University of Hong Kong; Hong Kong: 2003. 
• 7b Ko YY. Cheng KF. Chiu P. Book of Abstracts   The 23rd International Symposium on the Chemistry of Natural Products, IUPAC; Florence, Italy: 2002.  p.P118 
• Recently, an intermolecular cycloaddition of a carbene-generated carbonyl ylide with propadiene in the context of a total synthesis of nemorensic acid has been reported:
• 8a Hodgson DM. Le Strat F. Chem. Commun.  2004,  822 
• 8b Hodgson DM. Le Strat F. Avery TD. Donohue AC. Brückl T. J. Org. Chem.  2004,  69:  8796 
• 9 Padwa A. Hornbuckle SF. Fryxell GE. Zhang ZJ. J. Org. Chem.  1992,  57:  5747 
• 10 Gras JL. Galledou BS. Bertrand M. Bull. Soc. Chim. Fr.  1988,  757 
• 11a Appendino G. Hoflack J. De Clercq PJ. Chiari G. Calleri M. Tetrahedron  1988,  44:  4605 
• 11b Finch H. Harwood LM. Highcock R. Jackson B. Prout K. Robertson G. Sewell RC. Synlett  1990,  384 
• 12 Lee HY. Sohn JH. Kim HY. Tetrahedron Lett.  2001,  42:  1695 
• 13 Crabbé P. Nassim B. Robert-Lopes MT. Org. Synth., Coll. Vol. VII  1990,  276 
• 14 Normant JF. Cahiez G. Alexakis A. Tetrahedron Lett.  1978,  33:  3013 
• 15 Bal BS. Childers WE. Pinnick HW. Tetrahedron  1981,  37:  2091 
• 16 Jefford CW. Kubota T. Zaslona A. Helv. Chim. Acta  1986,  69:  2048 
• 17 Holmquist CR. Roskamp EJ. J. Org. Chem.  1989,  54:  3258 
• 18a Baum JS. Shook DA. Davies HML. Smith HD. Synth. Commun.  1987,  17:  1709 
• 18b Davies HML. Cantrell WR. Romines KR. Baum JS. Org. Synth.  1992,  70:  93 

1

Present address: Xingxian Zhang, College of Pharmaceutical Science, Zhejiang University, P. R. of China.