Annulation of 2-Oxoalkylidenetriphenylphosphoranes with Enediones: A One-Step Synthesis of Substituted Cyclopentenones

Abstract

2-Oxoalkylidenetriphenylphosphoranes undergo [3+2] annulation with enediones to give cyclopentenones as major products along with cyclohexenones.

Key words

ylides - enediones - annulation - carbocycles - regioselectivity

References

• 2a Collins PW. Djuric SW. Chem. Rev.  1993,  93:  1533 
• 2b Rigby JH. In Comprehensive Organic Synthesis   Vol. 5:  Trost BM. Fleming I. Pergamon; Oxford: 1991.  p.626 
• 3a Himeda Y. Tanaka Y. Ueda I. Hatanaka M. J. Chem. Soc., Perkin Trans. 1  1998,  138 
• 3b Himeda Y. Yamataka Y. Ueda I. Hatanaka M. J. Org. Chem.  1997,  62:  6529 
• 3c Hatanaka M. Ishida A. Tanaka Y. Ueda I. Tetrahedron Lett.  1996,  37:  401 
• 3d Hatanaka M. Tanaka Y. Ueda I. Tetrahedron Lett.  1995,  36:  3719 
• 3e Hatanaka M. Himeda Y. Imashiro R. Tanaka Y. Ueda I. J. Org. Chem.  1994,  59:  111 
• 4 For cyclohexenone synthesis with α,β-unsaturated aldehydes, see: Pietrusiewicz KM. Monkiewicz J. Bodalski R. J. Org. Chem.  1983,  48:  788 
• 5 Yamanoi T. Akiyama T. Ishida E. Abe H. Amemiya M. Inazu T. Chem. Lett.  1989,  335 
• 6 Shevchuk MI. Volynskaya EM. Dombrovskii AV. Zh. Obshch. Khim.  1970,  40:  48 ; Chem. Abstr. 1970, 72, 100817
• 7 Wladislaw B. Marzorati L. Gruber J. Synth. Commun.  1990,  20:  2937 
• 8 Schuda PT. Ebner CB. Potlock SJ. Synthesis  1987,  1055 
• 9 Bell TW. Sondheimer F. J. Org. Chem.  1981,  46:  217 

1

New address: K. Matsumoto, Department of Chemistry, College of Science and Engineering, Meisei University, Hodokubo, Hino, Tokyo 191-8506, Japan.