A Modified and Highly Useful Protocol for the Bronsted Acid Catalyzed, Enantioselective, Vinylogous Mannich Reaction with Aliphatic Aldimines

被引：21

作者：

Abels, Falko ^{[1
]}

Schneider, Christoph ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2011年 / 24期

关键词：

vinylogous Mannich reaction; phosphoric acid; organocatalyis; contact ion pair; dienolate; BINOL; EFFICIENT;

D O I：

10.1055/s-0031-1289303

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantioselective as well as diastereoselective catalytic vinylogous Mannich reactions have been accomplished for the first time with aliphatic straight-chain aldimines and O,O-silylketene acetals and furnish valuable synthetic building blocks in high enantiomeric purity.

引用

页码：4050 / 4058

页数：9

共 29 条

[1]

Adair G, 2008, ALDRICHIM ACTA, V41, P31

[2] Stereodivergent diversity oriented synthesis of piperidine alkaloids [J].

Adriaenssens, Louis V. ;

Austin, Carolyn A. ;

Gibson, Mairi ;

Smith, David ;

Hartley, Richard C. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (22) :4998-5001

[3] Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid [J].

Akiyama, Takahiko ;

Honma, Yasuhiro ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :399-402

[4] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[5] CONVERSION OF N-ACYL-2,3-DIHYDRO-4-PYRIDONES TO 4-CHLORO-1,2-DIHYDROPYRIDINES USING THE VILSMEIER REAGENT - SYNTHESIS OF (-)-CONIINE AND (PLUS-OR-MINUS)-LUPININE [J].

ALAWAR, RS ;

JOSEPH, SP ;

COMINS, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7732-7739

[6] α,β-Unsaturated δ-lactones from copper-catalyzed asymmetric vinylogous Mukaiyama reactions of aldehydes:: Scope and mechanistic insights [J].

Bazan-Tejeda, Belen ;

Bluet, Guillaume ;

Broustal, Garance ;

Campagne, Jean-Marc .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (32) :8358-8366

[7] Vinylogous Mannich reactions: selectivity and synthetic utility [J].

Bur, SK ;

Martin, SF .

TETRAHEDRON, 2001, 57 (16) :3221-3242

[8] A highly efficient and practical method for catalytic asymmetric vinylogous Mannich (AVM) reactions [J].

Carswell, Emma L. ;

Snapper, Marc L. ;

Hoveyda, Amir H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7230-7233

[9] α,α-Dicyanoalkenes: versatile vinylogous nucleophiles for organic synthesis [J].

Cui, Hai-Lei ;

Chen, Ying-Chun .

CHEMICAL COMMUNICATIONS, 2009, (30) :4479-4486

[10] Lewis base activation of Lewis acids. Vinylogous aidol reactions [J].

Denmark, SE ;

Beutner, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7800-7801

← 1 2 3 →