Premium
Stereoselective Synthesis of 3‐Hydroxy‐4‐arylcyclopentanones and 4‐Arylcyclopentenones through a Heck–Matsuda Desymmetrization of meso cis ‐4‐Cyclopentene‐1,3‐diol
Author(s) -
Carmona Rafaela C.,
Correia Carlos Roque D.
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500281
Subject(s) - desymmetrization , chemistry , cyclopentene , enantioselective synthesis , heck reaction , diol , palladium , stereoselectivity , stereochemistry , organic chemistry , catalysis
A new palladium‐catalyzed route to 3‐hydroxy‐4‐arylcyclopentanones and 4‐arylcyclopentenones in a diastereo‐ and enantioselective manner by a Heck–Matsuda desymmetrization was achieved from the commercially available meso cis ‐4‐cyclopentene‐1,3‐diol. This method is highly practical, mild, high yielding and is carried out under “open vessel” conditions. Protected and unprotected substrates provide distinct products bearing considerable value as synthetic scaffolds for the synthesis of natural and unnatural bioactive compounds containing a five‐membered ring.