Cyclic sulfones from double conjugate addition of Rongalite

被引：1

作者：

Goga, Melina ^{[1
]}

Zong, Hao ^{[1
]}

Prana, Jazmine ^{[1
]}

Michel, Rudolph ^{[1
]}

Muro, Antonia ^{[1
]}

Rubin, Elana ^{[1
]}

Brenya, Janet ^{[1
]}

Bebbington, Magnus W. P. ^{[1
,2
]}

机构：

[1] Montclair State Univ, Coll Sci & Math, Dept Chem & Biochem, Montclair, NJ USA

[2] Montclair State Univ, Coll Sci & Math, Dept Chem & Biochem, Montclair, NJ 07043 USA

来源：

SYNTHETIC COMMUNICATIONS | 2023年 / 53卷 / 16期

基金：

美国国家科学基金会;

关键词：

Conjugate addition; dienones; Rongalite; sulfones; REAGENT;

D O I：

10.1080/00397911.2023.2222316

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic sulfones are obtained in up to 92% yield by double conjugate addition of Rongalite (sodium hydroxymethyl sulfinate) to dienones. The major product in each case is the kinetic trans-isomer of the 3,5-disubstituted ketosulfone. Eleven examples, including aryl and alkyl substituted substrates, are reported. The advantages of the method are its experimental simplicity, tolerance for both protic and oxidation-sensitive functional groups, and sterically challenging substrates. The work also significantly expands the scope of Rongalite as a conjugate nucleophile.

引用

页码：1351 / 1359

页数：9

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