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