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.

allenes - carbenoids - cyclization - cycloadditions - domino reactions

References and Notes

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

<A NAME="RW32605ST-2A">2a</A> Matsuda H. Morikawa T. Ninomiya K. Yoshikawa M. Tetrahedron  2001,  57:  8443 

<A NAME="RW32605ST-2B">2b</A> Matsuda H. Ninomiya K. Morikawa T. Yoshikawa M. Bioorg. Med. Chem. Lett.  1998,  8:  339 

<A NAME="RW32605ST-3A">3a</A> Padwa A. Hornbuckle SF. Chem. Rev.  1991,  91:  263 

<A NAME="RW32605ST-3B">3b</A> Padwa A. Weingarten MD. Chem. Rev.  1996,  96:  223 

<A NAME="RW32605ST-3C">3c</A> Padwa A. Chem. Commun.  1998,  1417 

<A NAME="RW32605ST-3D">3d</A> 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  

<A NAME="RW32605ST-4">4</A> Mehta G. Muthusamy S. Tetrahedron  2002,  58:  9477 

<A NAME="RW32605ST-5A">5a</A> Chiu P. Chen B. Cheng KF. Org. Lett.  2001,  3:  1721 

<A NAME="RW32605ST-5B">5b</A> Chen B. Ko RYY. Yuen MSM. Cheng KF. Chiu P. J. Org. Chem.  2003,  68:  4195 

<A NAME="RW32605ST-5C">5c</A> Chiu P. Pure Appl. Chem.  2005,  77:  1183 

<A NAME="RW32605ST-6">6</A> 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 

<A NAME="RW32605ST-7A">7a</A> Ko YY. PhD Dissertation   University of Hong Kong; Hong Kong: 2003. 

<A NAME="RW32605ST-7B">7b</A> 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:

<A NAME="RW32605ST-8A">8a</A> Hodgson DM. Le Strat F. Chem. Commun.  2004,  822 

<A NAME="RW32605ST-8B">8b</A> Hodgson DM. Le Strat F. Avery TD. Donohue AC. Brückl T. J. Org. Chem.  2004,  69:  8796 

<A NAME="RW32605ST-9">9</A> Padwa A. Hornbuckle SF. Fryxell GE. Zhang ZJ. J. Org. Chem.  1992,  57:  5747 

<A NAME="RW32605ST-10">10</A> Gras JL. Galledou BS. Bertrand M. Bull. Soc. Chim. Fr.  1988,  757 

<A NAME="RW32605ST-11A">11a</A> Appendino G. Hoflack J. De Clercq PJ. Chiari G. Calleri M. Tetrahedron  1988,  44:  4605 

<A NAME="RW32605ST-11B">11b</A> Finch H. Harwood LM. Highcock R. Jackson B. Prout K. Robertson G. Sewell RC. Synlett  1990,  384 

<A NAME="RW32605ST-12">12</A> Lee HY. Sohn JH. Kim HY. Tetrahedron Lett.  2001,  42:  1695 

<A NAME="RW32605ST-13">13</A> Crabbé P. Nassim B. Robert-Lopes MT. Org. Synth., Coll. Vol. VII  1990,  276 

<A NAME="RW32605ST-14">14</A> Normant JF. Cahiez G. Alexakis A. Tetrahedron Lett.  1978,  33:  3013 

<A NAME="RW32605ST-15">15</A> Bal BS. Childers WE. Pinnick HW. Tetrahedron  1981,  37:  2091 

<A NAME="RW32605ST-16">16</A> Jefford CW. Kubota T. Zaslona A. Helv. Chim. Acta  1986,  69:  2048 

<A NAME="RW32605ST-17">17</A> Holmquist CR. Roskamp EJ. J. Org. Chem.  1989,  54:  3258 

<A NAME="RW32605ST-18A">18a</A> Baum JS. Shook DA. Davies HML. Smith HD. Synth. Commun.  1987,  17:  1709 

<A NAME="RW32605ST-18B">18b</A> Davies HML. Cantrell WR. Romines KR. Baum JS. Org. Synth.  1992,  70:  93