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0142150733
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note
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For example, α-methylation of N-Boc-N-methyl phenylalanine derivatives proceeds in up to 82% ee, while that of the corresponding N-formyl-N-methyl derivative gives a racemic product; see ref 8a.
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23
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0142212829
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note
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Whereas α-methylation of N-Boc-N-methoxymethyl(MOM)-phenylalanine, -tyrosine, and -valine derivatives proceeds in 81%, 79%, and 87% ee, respectively (ref 8b), α-allylation of N-Boc-N-MOM-alanine derivative proceeds in 33% ee (unpublished data). The low ee in the reaction of an alanine derivative seems to be at least in part due to rapid racemization of the chiral enolate intermediate during intermolecular alkylation. On the other hand, the loss of enantiomeric purity of the chiral enolate is minimized during rapid five-membered intramolecular alkylation, and it gives 10 with high enantiomeric excess.
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24
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0344778061
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The stable conformers A and B of 1 were generated by a molecular modeling search with AMBER* force field with the GB/SA solvation model for water using MacroModel V 6.0. The difference in potential energies between A and B is estimated to be 0.1 kcal/mol. A PM3 calculation with a polarized continuum model (water, ε = 78.4) also gave stable structures similar to A and B: (a) Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129; (b) J. Comput. Chem. 1991, 12, 620.
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J. Am. Chem. Soc.
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Still, W.C.1
Tempczyk, A.2
Hawley, R.C.3
Hendrickson, T.4
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25
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84986439485
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The stable conformers A and B of 1 were generated by a molecular modeling search with AMBER* force field with the GB/SA solvation model for water using MacroModel V 6.0. The difference in potential energies between A and B is estimated to be 0.1 kcal/mol. A PM3 calculation with a polarized continuum model (water, ε = 78.4) also gave stable structures similar to A and B: (a) Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129; (b) J. Comput. Chem. 1991, 12, 620.
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