Tandem Chemoselective 1,2-/1,4-Migration of the Thio Group in Keto Thioesters: An Efficient Approach to Substituted Butenolides

被引：25

作者：

Mal, Kanchan ^{[1
]}

Naskar, Sandip ^{[1
]}

Sen, Shovan Kumar ^{[1
]}

Natarajan, Ramalingam ^{[1
]}

Das, Indrajit ^{[1
]}

机构：

[1] Indian Inst Chem Biol, CSIR, Organ & Med Chem Div, 4 Raja SC Mullick Rd, Kolkata 700032, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 20期

关键词：

heterocycles; isomerization; keto thioesters; rearrangement; sulfanyl group migration; SOLID-STATE PHOTOCHEMISTRY; VINYLOGOUS ALDOL REACTION; GAMMA-HYDROXYBUTENOLIDES; ALLENYL SULFIDES; NATURAL-PRODUCTS; RECENT PROGRESS; DERIVATIVES; MIGRATION; ANNULATION; FURANS;

D O I：

10.1002/adsc.201600640

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report herein an efficient and mechanistically unique tandem chemoselective 1,2-/1,4-migration of the thio group in keto thioesters that provides substituted butenolides in moderate to excellent yields. Thus, alpha-keto thioesters in the presence of stabilized phosphonate carbanions undergo tandem 1,2-sulfur migration; whereas 1,4-migration of the thio group has been achieved with the same thioesters after the treatment with Wittig reagents followed by BF3 center dot OEt2-catalyzed tandem reaction. The crossover experiments and the isolation of intermediates reveal a stepwise mechanism for both of these transformations.

引用

页码：3212 / 3230

页数：19

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