通过铜催化有机锌试剂的共轭加成实现功能化β,β-二取代和三取代乙烯基亚砜的高立体选择性合成。
Highly stereoselective synthesis of functionalized beta,beta-di- and trisubstituted vinylic sulfoxides by Cu-catalyzed conjugate addition of organozinc reagents.
作者信息
Maezaki Naoyoshi, Sawamoto Hiroaki, Suzuki Tomoko, Yoshigami Ryoko, Tanaka Tetsuaki
机构信息
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
出版信息
J Org Chem. 2004 Nov 26;69(24):8387-93. doi: 10.1021/jo048747l.
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.
通过铜催化有机锌试剂对手性1-炔基亚砜的共轭加成反应，合成了带有官能团的β,β-二取代手性烯基亚砜。由于官能化有机锌试剂的可得性以及反应的高顺式选择性，两种几何异构体的β,β-二取代烯基亚砜均被选择性地合成出来。此外，通过用亲电试剂捕获生成的α-亚磺酰基烯基碳负离子，1-炔基亚砜被衍生化为三取代烯基亚砜。借助该方法，通过分子内迈克尔加成反应，实现了高度非对映选择性的四氢呋喃（THF）和四氢吡喃（THP）环的形成。
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