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

被引：134

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

共 77 条

[1] Asymmetric Cycloadditions of o-Quinone Methides Employing Chiral Ammonium Fluoride Precatalysts [J].

Alden-Danforth, Ethan ;

Scerba, Michael T. ;

Lectka, Thomas .

ORGANIC LETTERS, 2008, 10 (21) :4951-4953

[2] Taming reactive phenol tautomers and o-quinone methides with transition metals:: A structure-reactivity relationship [J].

Amouri, H ;

Le Bras, J .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (07) :501-510

[3]

[Anonymous], 2014, ANGEW CHEM-GER EDIT

[4]

[Anonymous], ANGEW CHEM

[5]

[Anonymous], ANGEW CHEM

[6] N-acyl enamines in the Paterno-Buchi reaction: Stereoselective preparation of 1,2-amino alcohols by C-C bond formation [J].

Bach, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (08) :884-886

[7]

Bach T., 1996, Angewandte Chemie, V108, P976

[8] Neocandenatone, an isoflavan-cinnamylphenol quinone methide pigment from Dalbergia congestiflora [J].

Barragán-Huerta, BE ;

Peralta-Cruz, J ;

González-Laredo, RF ;

Karchesy, J .

PHYTOCHEMISTRY, 2004, 65 (07) :925-928

[9] Catalytic asymmetric Michael reactions with enamides as nucleophiles [J].

Berthiol, Florian ;

Matsubara, Ryosuke ;

Kawai, Nobuyuki ;

Kobayashi, Shu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (41) :7803-7805

[10] Enamides: valuable organic substrates [J].

Carbery, David R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3455-3460

← 1 2 3 4 5 6 7 8 →