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https://hdl.handle.net/10316/107442
Title: | Reactivity of steroidal 1-azadienes toward enamines: an approach to novel chiral penta- and hexacyclic steroids | Authors: | Lopes, Susana M. M. Santos, Joana R. C. Pinho e Melo, Teresa M. V. D. |
Issue Date: | 11-Feb-2021 | Publisher: | Royal Society of Chemistry | Project: | UIDP/00313/2020 UIDB/00313/2020 |
Serial title, monograph or event: | Organic & Biomolecular Chemistry | Volume: | 19 | Issue: | 5 | Abstract: | The chemical behavior of steroidal N-sulfonyl-1-azadienes toward carbonyl compounds, in the presence of pyrrolidine, is described. With aldehydes, these azadienes participate in hetero-Diels-Alder reactions with the in situ generated enamines. The stereoselectivity results from the approach of the dienophiles from the less hindered α-face of the steroid, with the pyrrolidine moiety endo and retention of the enamine trans geometry. This diastereoselective synthetic methodology led to a new class of chiral pentacyclic steroids. Interestingly, the studied steroidal scaffolds follow a different mechanistic pathway with cyclic ketones. They undergo a diastereoselective annulation reaction, under enamine catalysis, affording chiral hexacyclic steroids. | URI: | https://hdl.handle.net/10316/107442 | DOI: | 10.1039/d0ob02344b | Rights: | embargoedAccess |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
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File | Description | Size | Format | |
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Lopes2021OrgBiomolChem.pdf | 2.59 MB | Adobe PDF | View/Open |
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