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Synthesis of Enantiomerically Pure Bis‐Sulfinyl Substituted Phenylene Ethynylenes
Author(s) -
Barattucci Anna,
Chiara Aversa Maria,
Deni Elisa,
Papalia Teresa,
Bonaccorsi Paola
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400144
Subject(s) - chemistry , sonogashira coupling , epimer , sulfenic acid , phenylene , stereoselectivity , sulfoxide , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , palladium , catalysis , polymer , cysteine , enzyme
The stereoselective and efficient monoaddition of transient [(1 S ,2 R ,4 R )‐2‐hydroxy‐7,7‐dimethylbicyclo[2.2.1]hept‐1‐yl]methanesulfenic (=(1 S )‐isoborneol‐10‐sulfenic) acid to isomeric diethynylbenzenes affords {1‐[(1 S )‐isoborneol‐10‐sulfinyl]ethenyl}ethynylbenzenes. Their enantiomerically pure ( R S )‐epimers are involved in a Cu‐free Sonogashira coupling with 1,4‐diiodo‐2,5‐dimethoxybenzene to give C 2 ‐symmetric bis‐sulfinyl phenylene ethynylenes, stimulating prototypes of new sulfurated chiral architectures that can find application as chelating agents.