1 research outputs found
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 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 estersPeer reviewe