Abstract
The reaction of a symmetrical allylic dicarbonate or diacetate with a variety of β-keto esters in the presence of a palladium catalyst gave 2-substituted 5-vinyl-4,5-dihydrofuran-3-carboxylates, 4,6a-dihydro-3aH -cyclopenta[b ]furan-3-carboxylates, and 3a,4,5,7a-tetrahydrobenzofuran-3-carboxylates in moderate to good yields.
Key word
palladium catalyst - allylic substitution - tandem reaction - dihydrofuran - optical resolution
References
1a
Lipshutz BH.
Chem. Rev.
1986,
86:
795
1b
Nakanishi K.
Natural Products Chemistry
Kodansha;
Tokyo:
1974.
1c
The Chemistry of Heterocyclic Flavoring and Aroma Compounds
Vernin F.
Ellis Horwood;
Chichester:
1982.
1d
Kubo I.
Lee Y.-W.
Balogh-Nair V.
Nakanishi K.
Chapya A.
J. Chem. Soc., Chem. Commun.
1976,
949
2a
Harding KE.
Tiner HT. In
Comprehensive Organic Synthesis
Vol. 4:
Trost BM.
Fleming I.
Pergamon;
New York:
1991.
p.363
2b
Sargent MV.
Cresp TM. In
Comprehensive Organic Chemistry
Vol. 4:
Barton DHR.
Ollis DW.
Pergamon;
New York:
1979.
p.693
2c
Bird CW.
Cheesman GHW. In
Comprehensive Heterocyclic Chemistry
Vol. 4:
Katritzky AR.
Rees CW.
Pergamon;
New York:
1984.
Part 3.
3a
Vinogradov MG.
Kondorsky AE.
Nikishin GI.
Synthesis
1988,
60
3b
Barinelli LS.
Nicholas KM.
J. Org. Chem.
1988,
53:
2114
3c
Hayashi T.
Ohno A.
Lu S.
Matsumoto Y.
Fukuyo E.
Yanagi K.
J. Am. Chem. Soc.
1994,
116:
4221
3d
Yoshizaki H.
Satoh H.
Sato Y.
Nukui S.
Shibasaki M.
Mori M.
J. Org. Chem.
1995,
60:
2016
3e
Larock RC.
Yum EK.
Doty MJ.
Sham KKC.
J. Org. Chem.
1995,
60:
3270
3f
Bowman RK.
Johnson JS.
Org. Lett.
2006,
8:
573
3g
Tanimori S.
Kato Y.
Kirihata M.
Synthesis
2006,
865
4
Burgess K.
Tetrahedron Lett.
1985,
26:
3049
5
Zhang D.
Wu L.-Z.
Yang Q.-Z.
Li X.-H.
Zhang L.-P.
Tung C.-H.
Org. Lett.
2003,
5:
3221
6
Hutchings M.
Moffat D.
Simpkins NS.
Synlett
2001,
661
7
Antonioletti R.
Malancona S.
Cattaruzza F.
Bovicelli P.
Tetrahedron
2003,
59:
1673
8
Pearson AJ.
Khan MNI.
Clardy JC.
Cun-heng H.
J. Am. Chem. Soc.
1985,
107:
2748
9
Baciocchi E.
Ruzziconi R.
J. Org. Chem.
1986,
51:
1645
10
Tang E.
Huang X.
Xu W.-M.
Tetrahedron
2004,
60:
9963
11 According to our preliminary results, the corresponding chiral amides derived from either cyclic meso diacetate 3 or 5 with amide 8 were also separable on silica gel chromatography to afford diastereomerically pure (enantiomerically pure) dihydrofurans.