Bronsted Acid-Catalyzed, Highly Enantioselective Addition of Enamides to In Situ-Generated ortho-Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes

被引：133

作者：

Saha, Satyajit ^{[1
]}

Schneider, Christoph ^{[1
]}

机构：

[1] Univ Leipzig, Inst Organ Chem, D-04103 Leipzig, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 06期

关键词：

asymmetric catalysis; BrOnsted acids; domino reactions; organocatalysis; xanthenes; STRUCTURE-REACTIVITY RELATIONSHIPS; RING-CLOSING METATHESIS; FRIEDEL-CRAFTS REACTION; ASYMMETRIC-SYNTHESIS; C-C; NUCLEOPHILES; DERIVATIVES; ALKYLATION; AGENTS; DNA;

D O I：

10.1002/chem.201406044

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly enantioselective conjugate addition of enamides and enecarbamates to insitu-generated ortho-quinone methides, upon subsequent N,O-acetalization, gives rise to acetamido-substituted tetrahydroxanthenes with generally excellent enantio- and diastereoselectivities. A chiral BINOL-based phosphoric acid catalyst controls the enantioselectivity of the carbon-carbon bond-forming event. The products are readily converted into other xanthene-based heterocycles.

引用

页码：2348 / 2352

页数：5

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