Abstract
Oxazolidinethiones and thiazolidinethiones constitute a class of versatile chiral auxiliaries for asymmetric synthesis. Their easy preparation from readily available β-amino-alcohols and the high levels of asymmetric induction they provide make them excellent chiral auxiliaries useful for the preparation of chiral intermediates in the synthesis of natural products. These chiral auxiliaries have been utilized in a wide variety of synthetic transformations such as asymmetric aldol condensation, stereoselective alkylation of different electrophiles, stereoselective differentiation of enantiotopic groups in molecules bearing prochiral centers, and other interesting applications. This review attempts to summarize the preparation, synthetic applications, and cleavage of oxazolidinethiones and thiazolidinethiones, as well as the manipulation of chiral intermediates obtained in asymmetric transformations involving these chiral auxiliaries.
Keywords: asymmetric synthesis, oxazolidinethiones, thiazolidinethiones, asymmetric aldol additions, retronecine, discodermolide, salinomycin, altohyrtin, pateamine, decarestrictine, mycothiazole
Current Organic Chemistry
Title: The Application of Chiral Oxazolidinethiones and Thiazolidinethiones in Asymmetric Synthesis
Volume: 6 Issue: 4
Author(s): Francisco Velazquez and Horacio F. Olivo
Affiliation:
Keywords: asymmetric synthesis, oxazolidinethiones, thiazolidinethiones, asymmetric aldol additions, retronecine, discodermolide, salinomycin, altohyrtin, pateamine, decarestrictine, mycothiazole
Abstract: Oxazolidinethiones and thiazolidinethiones constitute a class of versatile chiral auxiliaries for asymmetric synthesis. Their easy preparation from readily available β-amino-alcohols and the high levels of asymmetric induction they provide make them excellent chiral auxiliaries useful for the preparation of chiral intermediates in the synthesis of natural products. These chiral auxiliaries have been utilized in a wide variety of synthetic transformations such as asymmetric aldol condensation, stereoselective alkylation of different electrophiles, stereoselective differentiation of enantiotopic groups in molecules bearing prochiral centers, and other interesting applications. This review attempts to summarize the preparation, synthetic applications, and cleavage of oxazolidinethiones and thiazolidinethiones, as well as the manipulation of chiral intermediates obtained in asymmetric transformations involving these chiral auxiliaries.
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Cite this article as:
Velazquez Francisco and Olivo F. Horacio, The Application of Chiral Oxazolidinethiones and Thiazolidinethiones in Asymmetric Synthesis, Current Organic Chemistry 2002; 6 (4) . https://dx.doi.org/10.2174/1385272024605023
DOI https://dx.doi.org/10.2174/1385272024605023 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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