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-
15
-
-
68349083872
-
-
Although we examined the 1,4- and 1,2-double nucleophilic addition using the imine protected with the TBS group, the 1,4-1,2 product was not obtained
-
Although we examined the 1,4- and 1,2-double nucleophilic addition using the imine protected with the TBS group, the 1,4-1,2 product was not obtained.
-
-
-
-
16
-
-
68349119597
-
-
When the 1,4- and 1,2-double nucleophilic addition with the α,β-unsaturated imine bearing an electron-withdrawing group was investigated, the 1,4-addition product was obtained instead of the 1,4-1,2 adduct
-
When the 1,4- and 1,2-double nucleophilic addition with the α,β-unsaturated imine bearing an electron-withdrawing group was investigated, the 1,4-addition product was obtained instead of the 1,4-1,2 adduct.
-
-
-
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17
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55949102066
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a) I. Mizota, Y Matsuda, I. Hachiya, M. Shimizu, Org. Lett. 2008, 10, 3977-3980;
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33747252279
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b) M. Shimizu, A. Takahashi, S. Kawai, Org. Lett. 2006, 8, 3585-3587;
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29344475803
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c) M. Shimizu, M. Kamiya, I. Hachiya, Chem. Lett. 2005, 34, 1456-1457;
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33749131818
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d) M. Shimizu, H. Kurokawa, A. Takahashi, Lett. Org. Chem, 2004, 1, 353-356;
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0028205241
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30
-
-
68349106186
-
-
Calculations were carried out by using the SPARTAN pro program. 6-3IG* calculations were also carried out by using MOPAC PC SPARTAN pro, Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvin, CA 926.12, USA, 1999.
-
Calculations were carried out by using the SPARTAN pro program. 6-3IG* calculations were also carried out by using MOPAC PC SPARTAN pro, Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvin, CA 926.12, USA, 1999.
-
-
-
-
31
-
-
68349119598
-
-
Results for the s-cis isomers are nearly the same as those for the s-trans; the difference in the method of calculation (HF/ STO-3G or PM3) has little influence on a qualitative conclusion.
-
Results for the s-cis isomers are nearly the same as those for the s-trans; the difference in the method of calculation (HF/ STO-3G or PM3) has little influence on a qualitative conclusion.
-
-
-
-
32
-
-
33746310614
-
-
For examples using silica gel. as a reaction promoter, see
-
For examples using silica gel. as a reaction promoter, see: M. Shimizu, M. Tanaka, T. Itho, I. Hachiya, Synlett 2006, 1687-1690.
-
(2006)
Synlett
, pp. 1687-1690
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-
Shimizu, M.1
Tanaka, M.2
Itho, T.3
Hachiya, I.4
-
33
-
-
68349103590
-
-
1H NMR spectroscopy that 1,4- and 1,2addition products 7ac, 7ad, and 7af were converted into 1,4 adducts by a retro-Strecker reaction (Table 7, Entries 3, 4, and 6). Because the adducts were not stable, the addition reactions with lb were not examined in detail.
-
1H NMR spectroscopy that 1,4- and 1,2addition products 7ac, 7ad, and 7af were converted into 1,4 adducts by a retro-Strecker reaction (Table 7, Entries 3, 4, and 6). Because the adducts were not stable, the addition reactions with lb were not examined in detail.
-
-
-
-
34
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34547424961
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a) W A. Maio, S. Sinishtaj, G. H. Posner, Org. Lett. 2007, 9, 2673-2676;
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11444250543
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0034612952
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0030986275
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0028901474
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42
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0024801303
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i) P. D. Bailey, R. D. Wilson, G. R. Brown, Tetrahedron Lett. 1989, 30, 6781-6784;
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-
44
-
-
33748661764
-
-
The regioselectivity of the addition of nucleophiles to α,β-unsaturated aldimines has been studied previously, see ref. For examples using α,β-unsaturated aldimines for the β-lactam synthesis, see: a
-
The regioselectivity of the addition of nucleophiles to α,β-unsaturated aldimines has been studied previously, see ref. For examples using α,β-unsaturated aldimines for the β-lactam synthesis, see: a) I. Fleming, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 1998, 2663-2671;
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(1998)
J. Chem. Soc. Perkin Trans. 1
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Fleming, I.1
Kilburn, J.D.2
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45
-
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0021170945
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b) D.-C. Ha, D. J. Hart, T.-K. Yang, J. Am. Chem. Soc. 1984, 106, 4819-4825.
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Ha, D.-C.1
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Yang, T.-K.3
-
46
-
-
68349108904
-
-
A control experiment was carried out by using acrolein as the substrate in place of the imine 1c. Under the conditions A in Table 8, the reaction gave the 1,4- and 1,2-addition product in 36% yield.
-
A control experiment was carried out by using acrolein as the substrate in place of the imine 1c. Under the conditions A in Table 8, the reaction gave the 1,4- and 1,2-addition product in 36% yield.
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-
-
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