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5
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0003417469
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B.M. Trost, I. Flemming, Pergamon New York, NY Chapter 3.3
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S.A. Godleski B.M. Trost, I. Flemming, Comprehensive Organic Synthesis Vol. 4 1991 Pergamon New York, NY Chapter 3.3
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(1991)
Comprehensive Organic Synthesis
, vol.4
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Godleski, S.A.1
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8
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84878229968
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3-allylpalladium complex
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3-allylpalladium complex
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14
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84878246954
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Preparation of 3
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Preparation of 3
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16
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0037213661
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H. Nemoto, X. Li, R. Ma, I. Suzuki, and M. Shibuya Tetrahedron Lett. 44 2003 73 75
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(2003)
Tetrahedron Lett.
, vol.44
, pp. 73-75
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Nemoto, H.1
Li, X.2
Ma, R.3
Suzuki, I.4
Shibuya, M.5
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17
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67650044561
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Protected Dicyanomethanol (H-MAC-R)
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H-MAC-Ac has been commercially available from Sigma-Aldrich since 2013
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H. Nemoto Protected Dicyanomethanol (H-MAC-R) Electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS) 2007: http://onlinelibrary.wiley.com/o/ eros/articles/rn00761/frame.html H-MAC-Ac has been commercially available from Sigma-Aldrich since 2013
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(2007)
Electronic Encyclopedia of Reagents for Organic Synthesis (E-EROS)
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Nemoto, H.1
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18
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0033547953
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H. Nemoto, T. Ibaragi, M. Bando, M. Kido, and M. Shibuya Tetrahedron Lett. 40 1999 1319 1322
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(1999)
Tetrahedron Lett.
, vol.40
, pp. 1319-1322
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Nemoto, H.1
Ibaragi, T.2
Bando, M.3
Kido, M.4
Shibuya, M.5
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19
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0000802637
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When a non-strained (not highly reactive) leaving group, such as an alkoxycarbonyl was used, 4 was not effective because the nucleophilicity of a Pd-phosphite complex is generally weaker than that of a phosphine complex. However, 4-methyl-3,5,8-trioxa-1-phosphabicyclo[2.2.2]octane (A), a tricyclic phosphine ligand, was effective
-
When a non-strained (not highly reactive) leaving group, such as an alkoxycarbonyl was used, 4 was not effective because the nucleophilicity of a Pd-phosphite complex is generally weaker than that of a phosphine complex. However, 4-methyl-3,5,8-trioxa-1-phosphabicyclo[2.2.2]octane (A), a tricyclic phosphine ligand, was effective: T. Takahashi, Y. Jinbo, K. Kitamura, and J. Tsuji Tetrahedron Lett. 25 1984 5921 5924
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(1984)
Tetrahedron Lett.
, vol.25
, pp. 5921-5924
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Takahashi, T.1
Jinbo, Y.2
Kitamura, K.3
Tsuji, J.4
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22
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0030767529
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H. Ohno, N. Mimura, A. Otaka, H. Tamamura, N. Fujii, and T. Ibuka Tetrahedron 53 1997 12933 12946
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(1997)
Tetrahedron
, vol.53
, pp. 12933-12946
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Ohno, H.1
Mimura, N.2
Otaka, A.3
Tamamura, H.4
Fujii, N.5
Ibuka, T.6
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23
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0002462212
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Sweeney et al. mainly reported the reaction of vinylaziridines with copper reagents. Thus, the detail of the palladium-catalyzed reaction, such as mol % of tetrakis(triphenylphosphine)palladium, temperature, or equivalents of diethyl malonate were not specified
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Sweeney et al. mainly reported the reaction of vinylaziridines with copper reagents. Thus, the detail of the palladium-catalyzed reaction, such as mol % of tetrakis(triphenylphosphine)palladium, temperature, or equivalents of diethyl malonate were not specified: A.A. Cantrill, N.A. Jarvis, I.M. Osborn, A. Ouadi, and B.J. Sweeney Synlett 1996 847 849
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(1996)
Synlett
, pp. 847-849
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Cantrill, A.A.1
Jarvis, N.A.2
Osborn, I.M.3
Ouadi, A.4
Sweeney, B.J.5
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24
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84878239515
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Synthetic application of a MAC reagent with palladium catalyst in high γ-selectivity according to Ref. 5 was reported. They mentioned that the unmasking step from the MAC moiety to carbonyl functionality proceeded in greater yield under milder conditions than the step for the acidic hydrolysis of the cyanide group
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Synthetic application of a MAC reagent with palladium catalyst in high γ-selectivity according to Ref. 5 was reported. They mentioned that the unmasking step from the MAC moiety to carbonyl functionality proceeded in greater yield under milder conditions than the step for the acidic hydrolysis of the cyanide group
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25
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59049090575
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K. Yamatsugu, L. Yin, S. Kamijo, Y. Kimura, M. Kanai, and M. Shibasaki Angew. Chem. 48 2008 1070 1076
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(2008)
Angew. Chem.
, vol.48
, pp. 1070-1076
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Yamatsugu, K.1
Yin, L.2
Kamijo, S.3
Kimura, Y.4
Kanai, M.5
Shibasaki, M.6
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27
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84878221678
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Active methylene and methyne compounds bearing a cyano group as an electron withdrawing group are known to be very palladium-affinitive nucleophiles
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Active methylene and methyne compounds bearing a cyano group as an electron withdrawing group are known to be very palladium-affinitive nucleophiles
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31
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4143123249
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N.T. Patil, I. Kadota, A. Shibuya, Y.S. Gyoung, and Y. Yamamoto Adv. Synth. Catal. 346 2004 800 804
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(2004)
Adv. Synth. Catal.
, vol.346
, pp. 800-804
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Patil, N.T.1
Kadota, I.2
Shibuya, A.3
Gyoung, Y.S.4
Yamamoto, Y.5
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32
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84878217294
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2 moiety is not highly acidic. Furthermore, they only examined triphenylphosphine but not 4.
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2 moiety is not highly acidic. Furthermore, they only examined triphenylphosphine but not 4.
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33
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84878217426
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2 (MAC reagents), which are smaller than 2-methylmalononitrile. Incidentally, the smallest active methyne must be hydrogen cyanide
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2 (MAC reagents), which are smaller than 2-methylmalononitrile. Incidentally, the smallest active methyne must be hydrogen cyanide.
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34
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33746385828
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H. Tamamura, M. Yamashita, Y. Nakajima, K. Sakano, A. Otaka, H. Ohno, T. Ibuka, and N. Fujii J. Chem. Soc., Perkin Trans. 1 1999 2983 2996
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(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 2983-2996
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Tamamura, H.1
Yamashita, M.2
Nakajima, Y.3
Sakano, K.4
Otaka, A.5
Ohno, H.6
Ibuka, T.7
Fujii, N.8
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35
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84878221268
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Although very high stereoselectivity was observed, the double inversion mechanism has been generally accepted. Therefore, the proposed mechanism for stereochemistry is illustrated in Supplementary data in order to focus the discussion on the regiochemistry
-
Although very high stereoselectivity was observed, the double inversion mechanism has been generally accepted. Therefore, the proposed mechanism for stereochemistry is illustrated in Supplementary data in order to focus the discussion on the regiochemistry.
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36
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0001342246
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H. Nemoto, R. Ma, H. Moriguchi, I. Suzuki, and M. Shibuya J. Organomet. Chem. 611 2000 445 448
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(2000)
J. Organomet. Chem.
, vol.611
, pp. 445-448
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Nemoto, H.1
Ma, R.2
Moriguchi, H.3
Suzuki, I.4
Shibuya, M.5
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37
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0034629433
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H. Nemoto, R. Ma, T. Ibaragi, I. Suzuki, and M. Shibuya Tetrahedron 56 2000 1463 1468
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(2000)
Tetrahedron
, vol.56
, pp. 1463-1468
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Nemoto, H.1
Ma, R.2
Ibaragi, T.3
Suzuki, I.4
Shibuya, M.5
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38
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0001409192
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K.A. Scheidt, H. Chen, B.C. Follows, S.R. Chemler, D.S. Coffey, and W.R. Roush J. Org. Chem. 63 1998 6436 6437
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(1998)
J. Org. Chem.
, vol.63
, pp. 6436-6437
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Scheidt, K.A.1
Chen, H.2
Follows, B.C.3
Chemler, S.R.4
Coffey, D.S.5
Roush, W.R.6
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39
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84878238619
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1H data for 15g-15j and 16g-16j, are available in Supplementary data
-
1H data for 15g-15j and 16g-16j, are available in Supplementary data.
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-
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40
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0001388469
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T. Ibuka, T. Taga, H. Habashita, K. Nakai, H. Tamamura, N. Fujii, Y. Chounan, H. Nemoto, and Y. Yamamoto J. Org. Chem. 58 1993 1207 1214
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(1993)
J. Org. Chem.
, vol.58
, pp. 1207-1214
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Ibuka, T.1
Taga, T.2
Habashita, H.3
Nakai, K.4
Tamamura, H.5
Fujii, N.6
Chounan, Y.7
Nemoto, H.8
Yamamoto, Y.9
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