2024-03-29T13:49:08Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1334082016-06-28T01:06:09Zcom_10261_38com_10261_5col_10261_291
2016-06-14T09:10:14Z
urn:hdl:10261/133408
Highly Stereoselective Synthesis and Hydrogenation of (Z)‑1-Alkyl-2- arylvinyl Acetates: a Wide Scope Procedure for the Preparation of Chiral Homobenzylic Esters
González-Liste, Pedro J.
León, Félix
Arribas, Inmaculada
Rubio Moreno, Miguel
García-Garrido, Sergio E.
Cadierno, Victorio
Pizzano, Antonio
Iodo-alkenes
Enol esters
Asymmetric hydrogenation
Chiral esters
Rh catalysts
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
2016-06-14T09:10:14Z
2016-06-14T09:10:14Z
2016
artículo
ACS Catalysis, 6: 3056-3060 (2016)
http://hdl.handle.net/10261/133408
10.1021/acscatal.6b00282
eng
Publisher's version
http://dx.doi.org/10.1021/acscatal.6b00282
Sí
Creative Commons Attribution License
openAccess
American Chemical Society