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34447501379
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A single example using an α,β-unsaturated aldehyde was reported, see
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Ref1
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29
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0033606865
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2-(Trimethylsilyl)vinylketene has been reported to be a remarkable stable vinylketene and has been used for non-enantioselective HDA reactions
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43
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34447510557
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-
2NHEt]Cl is formed.
-
2NHEt]Cl is formed.
-
-
-
-
44
-
-
13644264785
-
-
Yield of 6a: 55-76, decreasing values in this order: M, Er III, SnII, ScIII, NdIII, In III, CuII, YbIII, LiI, Sm III, ZrIV, AlIII, MgII, Gd III, BiIII, EuIII, ZnII, Y III. The combination of cinchona alkaloid derivatives and metal triflate salts was previously successfully applied to [2+2] cycloadditions of ketenes. See: S. France, M. H. Shah, A. Weatherwax, H. Wack, J. P. Roth, T. Lectka, J. Am. Chem. Soc. 2005, 127, 1206 and Ref, 18e
-
III. The combination of cinchona alkaloid derivatives and metal triflate salts was previously successfully applied to [2+2] cycloadditions of ketenes. See: S. France, M. H. Shah, A. Weatherwax, H. Wack, J. P. Roth, T. Lectka, J. Am. Chem. Soc. 2005, 127, 1206 and Ref. [18e].
-
-
-
-
45
-
-
34447538835
-
-
The absolute configuration of δ-lactone 6f was determined by chemical correlation. For details see the Supporting Information.
-
The absolute configuration of δ-lactone 6f was determined by chemical correlation. For details see the Supporting Information.
-
-
-
-
47
-
-
34447518088
-
-
Theoretical studies of HAD reactions have revealed that the mechanism can change from a concerted nonsynchronous to a stepwise mechanism depending on the substituents on the reacting species and on the reaction conditions. See for example: a L. F. Tietze, J. Fennen, E. Anders, Angew. Chem. 1989, 101, 1420;
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Theoretical studies of HAD reactions have revealed that the mechanism can change from a concerted nonsynchronous to a stepwise mechanism depending on the substituents on the reacting species and on the reaction conditions. See for example: a) L. F. Tietze, J. Fennen, E. Anders, Angew. Chem. 1989, 101, 1420;
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49
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53
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37049105516
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Based on literature precedent for the hydrolysis of β- trichloromethyl-β-lactones (H. Wynberg, E. G. J. Staring, J. Chem. Soc. Chem. Commun. 1984, 1181)
-
Based on literature precedent for the hydrolysis of β- trichloromethyl-β-lactones (H. Wynberg, E. G. J. Staring, J. Chem. Soc. Chem. Commun. 1984, 1181)
-
-
-
-
54
-
-
3042839768
-
-
N2 ring opening. Oxidation of primary alcohol 10 providing 7 revealed the same configuration for 10 (see the Supporting Information).
-
N2 ring opening. Oxidation of primary alcohol 10 providing 7 revealed the same configuration for 10 (see the Supporting Information).
-
-
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55
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0029052235
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C. E. Song, J. K. Lee, S. H. Lee, S. Lee, Tetrahedron: Asymmetry 1995, 6, 1063.
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56
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24944510411
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For the synthetic usefulness of dichloromethyl groups see e.g, a
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For the synthetic usefulness of dichloromethyl groups see e.g.: a) K.-i. Sato, S. Akai, N. Sugita, T. Ohsawa, T. Kogure, H. Shoji, J. Yoshimura, J. Org. Chem. 2005, 70, 7496;
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1442360066
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58
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0242558389
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59
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0037205011
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See Ref. [23] and a M. E. Jung, G. Piizzi, J. Org. Chem. 2002, 67, 3911;
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See Ref. [23] and a) M. E. Jung, G. Piizzi, J. Org. Chem. 2002, 67, 3911;
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60
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0037068147
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K. Tamao, T. Kakui, M. Akita, T. Iwahara, R. Kanatani, J. Yoshida, M. Kumada, Tetrahedron 1983, 39, 983.
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Kumada, M.7
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62
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34447516295
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The relative configuration of 13 was assigned by NOE experiments: see the Supporting Information for details.
-
The relative configuration of 13 was assigned by NOE experiments: see the Supporting Information for details.
-
-
-
-
63
-
-
34447519704
-
-
Product 11 is a mixture of three compounds with different groups X, which can be F, OH, or an O bridge in a dimeric species.
-
Product 11 is a mixture of three compounds with different groups X, which can be F, OH, or an O bridge in a dimeric species.
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