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(i) Kitagawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y.; Taguchi, T. J. Org. Chem. 1998, 63, 9470-9475.
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0034693301
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0028244852
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For allene, see: (a) Besson, L.; Bazin, J.; Gore, J.; Cazes, B. Tetrahedron Lett. 1994, 35, 2881-2884.
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0000903824
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(b) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019-6020.
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0030574040
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and references therein
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(d) Meguro, M.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 7453-7456 and references therein.
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Meguro, M.1
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21
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22944443399
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Krause, N., Stephen, A., Hashmi, K., Eds.; Wiley-VCH: Weinheim
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Ma, S. In Modern Allene Chemistry; Krause, N., Stephen, A., Hashmi, K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, pp 595-684.
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Ma, S.1
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22
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37049087954
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Parsons and co-workers reported the intramolecular Michael-type reaction of allene derivative with a terminal carbanion species. Thus, the ring-closing reaction of dimethyl 4-methyl-6-(phenylsulfinyl)-4,5-hexadiene-1,1-dicarboxylate resulted in the formation of seven-membered oxacycles, instead of the expected carbocycles, presumably due to exo-mode closure by the oxygen atom of the methoxycarbonyl moiety at the sp-hybridized carbon center. The cyclopentane derivative, which would be anticipated by the attack of the terminal carbanion moiety in an exo-mode manner, could not be detected. Pairaudeau, G.; Parsons, P. J.; Underwood, J. M. Chem. Commun. 1987, 1718-1720.
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Pairaudeau, G.1
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Underwood, J.M.3
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24
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-
0037148995
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-
The intermolecular Michael-type reaction between the 1,2-allenyl ketones with the active methine derivatives has been reported. Ma, S.; Yin, S.; Li, L.; Tao, F. Org. Lett. 2002, 4, 505-507.
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0035909599
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Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385-3387.
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Mukai, C.1
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26
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37049087954
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Parsons reported an exo-mode ring-closing reaction of allenyl sulfoxide derivatives; see: (a) Pairaudeau, G.; Parsons, P. J.; Underwood, J. M. J. Chem. Soc., Chem. Commun. 1987, 1718-1720.
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(e) Edwards, N.; Macritchie, J. A.; Parsons, P. J.; Drew, M. G. B.; Jahans, A. W. Tetrahedron 1997, 53, 12651-12660.
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(f) Edwards, N.; Macritchie, J. A.; Parsons, P. J. Tetrahedron Lett. 1998, 39, 3605-3608.
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Edwards, N.1
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Parsons, P.J.3
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32
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0032497686
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Dai described an exo-mode ring-closing reaction of allenyl sulfones resulting in the formation of five-membered oxacycles: Dai, W.-M.; Lee, M. Y. H. Tetrahedron 1998, 54, 12497-12512.
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Dai, W.-M.1
Lee, M.Y.H.2
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4644319585
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Mukai, C.; Ohta, M.; Yamashita, H.; Kitagaki, S. J. Org. Chem. 2004, 69, 6867-6873.
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Mukai, C.1
Ohta, M.2
Yamashita, H.3
Kitagaki, S.4
-
34
-
-
0000450013
-
-
An endo-mode ring-closing reaction of trisubstituted allenylphosphine oxides, leading to the dihydrofuran skeleton, has been reported: Pravia, K.; White, R.; Fodda, R.; Maynard, D. F. J. Org. Chem. 1996, 61, 6031-6032.
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Pravia, K.1
White, R.2
Fodda, R.3
Maynard, D.F.4
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35
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0034915899
-
-
Brel reported an exo-mode cyclization of the allenyl phosphonate derivatives leading to a furan framework: Brel, V. K. Synthesis 2001, 1539-1545.
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Synthesis
, pp. 1539-1545
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Brel, V.K.1
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36
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1642339008
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Mukai, C.; Kobayashi, M.; Kubota, S.; Takahashi, Y.; Kitagaki, S. J. Org. Chem. 2004, 69, 2128-2136.
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Mukai, C.1
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Kubota, S.3
Takahashi, Y.4
Kitagaki, S.5
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37
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0037450464
-
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Part of this work was published as a preliminary communication: Mukai, C.; Ukon, R.; Kuroda, N. Tetrahedron Lett. 2003, 44, 1583-1586.
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Mukai, C.1
Ukon, R.2
Kuroda, N.3
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38
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0017880611
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(a) Corey, E. J.; Niwa, H.; Knolle, J. J. Am. Chem. Soc. 1978, 100, 1942-1943.
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Corey, E.J.1
Niwa, H.2
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39
-
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0001066504
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(b) Mukai, C.; Nomura, I.; Yamanishi, K.; Hanaoka, M. Org. Lett. 2002, 4, 1755-1758.
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Mukai, C.1
Nomura, I.2
Yamanishi, K.3
Hanaoka, M.4
-
42
-
-
33544460284
-
-
note
-
tBuOH and THF (1:1) was used for this compound due to its solubility.
-
-
-
-
43
-
-
33544459544
-
-
note
-
Allenes 14 were prepared from the hexynyl iodide derivatives 12 via the corresponding active methine derivatives 13 (see the Supporting Information).
-
-
-
-
44
-
-
33544464063
-
-
note
-
Compounds 7e and 14e were prepared according to the general procedure (see the Supporting Information).
-
-
-
-
45
-
-
33544466367
-
-
note
-
Compound 28 was prepared from the known dimethyl malonate derivative 26 (see the Supporting Information).
-
-
-
-
46
-
-
33544465376
-
-
note
-
1H NMR spectral analysis.
-
-
-
-
47
-
-
33544469419
-
-
note
-
1H NMR spectral analysis.
-
-
-
-
48
-
-
33544458098
-
-
note
-
Compound 29 was prepared from the known dimethyl malonate derivative 27 (see the Supporting Information).
-
-
-
-
49
-
-
33544461001
-
-
note
-
Allenes 39-41 were prepared from the corresponding alkynes 33-35 via compounds 36-38 (see the Supporting Information).
-
-
-
-
50
-
-
33544460176
-
-
note
-
The (E)-stereochemistry of 42a, 43a, and 44a was determined by an NOE experiment. For instance, 1.4% enhancement of Ha of 43a was observed upon irradiation of a vinyl proton.
-
-
-
-
51
-
-
33544461245
-
-
note
-
tBuOLi for 5 min.
-
-
-
-
52
-
-
33544469529
-
-
note
-
tBuOLi for 5 min.
-
-
-
-
53
-
-
33544457550
-
-
note
-
The (Z)-stereochemistry of 42b, 43b, and 44b was confirmed as follows. Treatment of 42b, for example, with DDQ afforded the allylic alcohol derivative 45 in 91% yield. An NOE experiment of 45 revealed a 9% enhancement of Ha when allylic protons were irradiated.
-
-
-
-
54
-
-
33544455088
-
-
note
-
Compounds 47 and 48 were obtained as a mixture of two diastereoisomers in a ratio of ca. 1:1.
-
-
-
-
55
-
-
33544455266
-
-
note
-
Compound 51 was prepared form the known iodobenzene derivative 49 via the propargyl alcohol derivative 50 (see the Supporting Information).
-
-
-
|