Highly stereoselective synthesis of functionalized beta,beta-di- and trisubstituted vinylic sulfoxides by Cu-catalyzed conjugate addition of organozinc reagents.
beta,beta-Disubstituted chiral vinylic sulfoxides bearing functionalities have been synthesized via Cu-catalyzed conjugate addition of organozinc reagents to chiral 1-alkynyl sulfoxides. Due to the availability of functionalized organozinc reagents and high syn-selectivity of the reaction, both geometric beta,beta-disubstituted vinylic sulfoxides were selectively synthesized. Furthermore, 1-alkynyl sulfoxides were derivatized into trisubstituted vinylic sulfoxides by trapping the resulting alpha-sulfinyl vinylic carbanion with electrophiles. Highly diastereoselective THF and THP ring formations were accomplished by means of this methodology followed by an intramolecular Michael addition.
Maezaki
Naoyoshi
N
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Sawamoto
Hiroaki
H
Suzuki
Tomoko
T
Yoshigami
Ryoko
R
Tanaka
Tetsuaki
T