Direct Enantioselective Bronsted Acid Catalyzed N-Acyliminium Cyclization Cascades of Tryptamines and Ketoacids

被引：123

作者：

Holloway, Chloe A. ^{[2
]}

Muratore, Michael E. ^{[1
]}

Storer, R. Ian ^{[3
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[3] Pfizer Global Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

ACCESS;

D O I：

10.1021/ol101651t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct enantio- and diastereoselective N-acyliminium cyclization cascade through chiral phosphoric acid catalyzed condensation of tryptamines with gamma- and delta-ketoacid derivatives to provide architecturally complex heterocycles has been developed. The reaction is technically simple to perform, atom-efficient, and broad in scope. Employing 10 mol % of (R)-BINOL derived chiral phosphoric acids in refluxing toluene allowed the polycyclic product materials to be generated in good yields (53-99%) and moderate to high enantioselectivities (68-98% ee).

引用

页码：4720 / 4723

页数：4

共 33 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[2] Stronger bronsted acids [J].

Akiyama, Takahiko .

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

[3] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[4] A Formal Synthesis of Porantheridine and an Epimer [J].

Bates, Roderick W. ;

Lu, Yongna .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9460-9465

[5] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

[6] Asymmetric organocatalytic domino reactions [J].

Enders, Dieter ;

Grondal, Christoph ;

Huettl, Matthias R. M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581

[7] A Flexible Approach to Grandisine Alkaloids: Total Synthesis of Grandisines B, D, and F [J].

Kurasaki, Haruaki ;

Okamoto, Iwao ;

Morita, Nobuyoshi ;

Tamura, Osamu .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) :12754-12763

[8] Chiral Phosphoric Acid Catalyzed Addition of Dihydropyrans to N-Acyl Imines: Stereocontrolled Access to Enantioenriched Spirocyclic Oxazoletetrahydropyrans with Three Contiguous Stereocenters [J].

Li, Guilong ;

Kaplan, Matthew J. ;

Wojtas, Lukasz ;

Antilla, Jon C. .

ORGANIC LETTERS, 2010, 12 (09) :1960-1963

[9] Cyclizations of N-acyliminium ions [J].

Maryanoff, BE ;

Zhang, HC ;

Cohen, JH ;

Turchi, IJ ;

Maryanoff, CA .

CHEMICAL REVIEWS, 2004, 104 (03) :1431-1628

[10] Total synthesis of the alkaloid (±)-aspidophytine based on carbonyl ylide cycloaddition chemistry [J].

Mejia-Oneto, Jose M. ;

Padwa, Albert .

HELVETICA CHIMICA ACTA, 2008, 91 (02) :285-302

← 1 2 3 4 →