Highly stereoselective synthesis of functionalized β,β-Di- and trisubstituted vinylic sulfoxides by Cu-catalyzed conjugate addition of organozinc reagents

被引：23

作者：

Maezaki, N ^{[1
]}

Sawamoto, H ^{[1
]}

Suzuki, T ^{[1
]}

Yoshigami, R ^{[1
]}

Tanaka, T ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 24期

关键词：

D O I：

10.1021/jo048747l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：8387 / 8393

页数：7

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