Highly Stereoselective Synthesis and Hydrogenation of (Z)‑1-Alkyl-2- arylvinyl Acetates: a Wide Scope Procedure for the Preparation of Chiral Homobenzylic Esters
A synthesis of (Z)-1-alkyl-2-arylvinyl acetates 3 with broad scope is reported by using two complementary methods. The first one uses a stereospecific gold-catalyzed addition of acetic acid to 1-iodo-alkynes, followed by a Suzuki coupling. By the second, 1-methyl-2-arylvinyl substrates have been obt...
| Autores: | , , , , , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2016 |
| País: | España |
| Recursos: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/133408 |
| Acesso em linha: | http://hdl.handle.net/10261/133408 |
| Access Level: | acceso abierto |
| Palavra-chave: | Iodo-alkenes Enol esters Asymmetric hydrogenation Chiral esters Rh catalysts |
| Resumo: | A synthesis of (Z)-1-alkyl-2-arylvinyl acetates 3 with broad scope is reported by using two complementary methods. The first one uses a stereospecific gold-catalyzed addition of acetic acid to 1-iodo-alkynes, followed by a Suzuki coupling. By the second, 1-methyl-2-arylvinyl substrates have been obtained selectively as the Z isomers by O-acylation of enolates of methyl benzyl ketones. In addition, the asymmetric hydrogenation of enol esters 3 has been covered for the first time. Using rhodium catalysts based on chiral phosphinephosphite ligands (P-OP), highly enantioselective hydrogenations (up to 99% ee) have been achieved for a wide range of substrates. Thus, the synthesis and enantioselective hydrogenation of 3 provides a convenient and versatile procedure for the synthesis of valuable chiral homobenzylic esters |
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