Upon treatment with the metal enolates of methylene active compounds (dimethyl malonate and dibenzoylmethane) (C-nucleophiles) and benzyl carbamate (N-nucleophile), D-allal- and D-galactal-derived vinyl epoxides are stereoselectively transformed, in a single step, into diastereoisomeric, highly functionalized, enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans. (C) 2019 Elsevier Ltd. All rights reserved.
Enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans from D-allal- and D-galactal-derived vinyl epoxides / V. Di Bussolo, S. Princiotto, V. Bordoni, E. Martinelli, L. Favero, S. Crotti, G. Uccello Barretta, F. Balzano, M. Pineschi, P. Crotti. - In: TETRAHEDRON. - ISSN 0040-4020. - 75:33(2019 Aug 16), pp. 4425-4443. [10.1016/j.tet.2019.06.003]
Enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans from D-allal- and D-galactal-derived vinyl epoxides
S. PrinciottoSecondo
;
2019
Abstract
Upon treatment with the metal enolates of methylene active compounds (dimethyl malonate and dibenzoylmethane) (C-nucleophiles) and benzyl carbamate (N-nucleophile), D-allal- and D-galactal-derived vinyl epoxides are stereoselectively transformed, in a single step, into diastereoisomeric, highly functionalized, enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans. (C) 2019 Elsevier Ltd. All rights reserved.
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