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(b) This approach, based on Husson's methodology first developed in the piperazine series, has been applied afterwards in the tetrahydroisoquinoline series as well. Roussi, F.; Quirion, J. C.; Tomas, A.; Husson, H. P. Tetrahedron 1998, 54, 10363.
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This comparison has been done by Davies and Seebach in the course of studies related to diastereoselective alkylation and protonation of lithium enolates derived from chiral imidazolidinones or diketopiperazines. In both examples, whether alkyl halides or various proton sources are used to quench the corresponding enolates, the same diastereofacial selectivity is observed, see: Bull, S. D.; Davies, S. G.; Epstein, S. W.; Ouzman, J. V. A. Tetrahedron: Asymmetry 1998, 9, 2795. Seebach, D.; Dziadulewicz, E.; Behrendt, L.; Cantoreggi, S.; Fitzi, R. Liebigs Ann. Chem. 1989, 1215.
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This comparison has been done by Davies and Seebach in the course of studies related to diastereoselective alkylation and protonation of lithium enolates derived from chiral imidazolidinones or diketopiperazines. In both examples, whether alkyl halides or various proton sources are used to quench the corresponding enolates, the same diastereofacial selectivity is observed, see: Bull, S. D.; Davies, S. G.; Epstein, S. W.; Ouzman, J. V. A. Tetrahedron: Asymmetry 1998, 9, 2795. Seebach, D.; Dziadulewicz, E.; Behrendt, L.; Cantoreggi, S.; Fitzi, R. Liebigs Ann. Chem. 1989, 1215.
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(a) Our results, therefore, find analogy in the work of Askin. Indeed, alkylation of prolinol amide enolates with alkyl halides and epoxides takes place with opposite diastereoselectivity. This finding is interpreted by the author by an intermolecular chelation of the epoxide with the lithium alkoxide, see: Askin, D.; Volante, R. P.; Ryan, K. M. Tetrahedron lett. 1988, 29, 4245.
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