On-Water Vinylogous Mukaiyama-Michael Addition of Heterocyclic 2-Silyloxydienes to 1,2-Diaza-1,3-dienes: One-Pot Three-Step Entry to Functionality-Rich Pyrroles

被引：17

作者：

Battistini, Lucia ^{[1
]}

Dell'Amico, Luca ^{[1
]}

Sartori, Andrea ^{[1
]}

Curti, Claudio ^{[1
]}

Pelosi, Giorgio ^{[2
]}

Casiraghi, Giovanni ^{[1
]}

Attanasi, Orazio A. ^{[3
]}

Favi, Gianfranco ^{[3
]}

Zanardi, Franca ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Farmaceut, I-43124 Parma, Italy

[2] Univ Parma, Dipartimento Chim Gen & Inorgan, I-43124 Parma, Italy

[3] Univ Urbino, Ist Chim Organ, I-61029 Urbino, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 11-12期

关键词：

1,2-diaza-1,3-dienes; green chemistry; nitrogen heterocycles; silyloxydienes; vinylogous Mukaiyama-Michael reaction; PROMOTED ORGANIC-REACTIONS; DIELS-ALDER REACTIONS; SILYL ENOL ETHERS; HYDROPHOBIC SURFACES; CARBONYL-COMPOUNDS; AQUEOUS-MEDIA; ACID; KETONES; CATALYSIS; ALDOL;

D O I：

10.1002/adsc.201100296

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Densely substituted pyrrole-carboxylates have been prepared in good yields in a highly practical one-pot three-step procedure. The key reaction of this process, which involves an uninterrupted sequence of reactions on-water, is a diastereoselective vinylogous Mukaiyama-Michael addition reaction (VMMcR) of heterocyclic 2-silyloxydienes to 1,2-diaza-1,3-dienes mediated by water itself. Subsequent in situ addition of catalytic aqueous sodium carbonate promotes an intramolecular aza-Michael addition with final ring-opening and aromatization. The superior use of water in the VMMcR as both reaction medium and promoter vis-a-vis deployment of conventional Lewis acids in organic solvents is highlighted, which provides the best results in terms of reaction rate, efficiency, stereoselectivity, and overall practicality.

引用

页码：1966 / 1972

页数：7

共 61 条

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[2]

2-S

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