Asymmetric Synthesis of Secondary and Tertiary Propargylic Alcohols by Umpolung of Acetylenic Sulfones and ortho-Sulfinyl Carbanions
| Autor: | Rubén Sánchez-Obregón, Ricardo I. Rodríguez, Elsie Ramírez, José Alemán, Francisco Yuste |
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| Přispěvatelé: | UAM. Departamento de Química Orgánica |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Steric effects
Ions 010405 organic chemistry Organic Chemistry Enantioselective synthesis Substituent Ether Química 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Umpolung Addition reactions chemistry.chemical_compound chemistry Alcohols Propargyl Moiety Crown ethers Carbanion |
| Zdroj: | Biblos-e Archivo. Repositorio Institucional de la UAM instname |
| ISSN: | 2015-6456 |
| Popis: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.joc.7b02887 The generation of diastereomerically enriched secondary benzyl propargyl alcohols by the asymmetric addition of ortho-sulfinylbenzyl carbanions to sulfonylacetylene derivatives via formation of a Csp-Csp 3 bond is described. This reaction proceeds through an unusual α-attack (anti-Michael addition) of the ortho-sulfinylbenzyl carbanions, followed by elimination of the arylsulfonyl moiety. The scope of this alkynylation reaction is also discussed. Moreover, the development of a new approach for the synthesis of optically active tertiary benzylpropargyl alcohols is described, discussing the possible stereocourse of the reaction so as the influence of the ether 18-crown-6 and steric importance of acetylenic substituent We thank DGAPA-UNAM (project number PAPIITIN205316) for financial support. Financial support from the Spanish Government (CTQ2015-64561-R) is also gratefully acknowledged |
| Databáze: | OpenAIRE |
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