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Title

Highly Stereoselective Synthesis and Hydrogenation of (Z)‑1-Alkyl-2- arylvinyl Acetates: a Wide Scope Procedure for the Preparation of Chiral Homobenzylic Esters

AuthorsGonzález-Liste, Pedro J.; León, Felix; Arribas, Inmaculada ; Rubio Moreno, Miguel ; García-Garrido, Sergio E.; Cadierno, Victorio; Pizzano, Antonio
KeywordsIodo-alkenes
Enol esters
Asymmetric hydrogenation
Chiral esters
Rh catalysts
Issue Date2016
PublisherAmerican Chemical Society
CitationACS Catalysis, 6: 3056-3060 (2016)
AbstractA 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
Publisher version (URL)http://dx.doi.org/10.1021/acscatal.6b00282
URIhttp://hdl.handle.net/10261/133408
DOI10.1021/acscatal.6b00282
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