Sulfoxide-Directed Enantioselective Synthesis of Functionalized Tetrahydropyridines

被引：19

作者：

Fernandez de la Pradilla, Roberto ^{[1
]}

Simal, Carmen ^{[1
]}

Bates, Robert H. ^{[1
]}

Viso, Alma ^{[1
]}

Infantes, Lourdes ^{[2
]}

机构：

[1] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

[2] CSIC, Inst Quim Fis Rocasolano, E-28006 Madrid, Spain

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 19期

关键词：

DIELS-ALDER REACTIONS; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED PIPERIDINES; ASYMMETRIC-SYNTHESIS; CYCLOADDITION; (+)-SEDAMINE;

D O I：

10.1021/ol402141d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly selective base-promoted cyclization of enantiopure sulfinyl dienamines provides stereodefined sulfinyl 1,2,3,6-tetrahydropyridines (dr up to 99:1). Subsequent sigmatropic rearrangement affords tetrahydropyridin-3-ols in good yields and selectivities.

引用

页码：4936 / 4939

页数：4

共 45 条

[1] Diels-Alder reactions of 1-azadienes [J].

Behforouz, M ;

Ahmadian, M .

TETRAHEDRON, 2000, 56 (30) :5259-5288

[2] 3-Aminopiperidine-Based Peptide Analogues as the First Selective Noncovalent Inhibitors of the Bacterial Cysteine Protease IdeS [J].

Berggren, Kristina ;

Vindebro, Reine ;

Bergstrom, Claes ;

Spoerry, Christian ;

Persson, Helena ;

Fex, Tomas ;

Kihlberg, Jan ;

von Pawel-Rammingen, Ulrich ;

Luthmant, Kristina .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (06) :2549-2560

[3]

Buffat M. G. P., 2004, TETRAHEDRON, V60, P1701

[4] Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines [J].

Bull, James A. ;

Mousseau, James J. ;

Pelletier, Guillaume ;

Charette, Andre B. .

CHEMICAL REVIEWS, 2012, 112 (05) :2642-2713

[5] Recent developments in imino Diels-Alder reactions [J].

Buonora, P ;

Olsen, JC ;

Oh, T .

TETRAHEDRON, 2001, 57 (29) :6099-6138

[6] Enantiopure sulfoxides: recent applications in asymmetric synthesis [J].

Carmen Carreno, M. ;

Hernandez-Torres, Gloria ;

Ribagorda, Maria ;

Urbano, Antonio .

CHEMICAL COMMUNICATIONS, 2009, (41) :6129-6144

[7] A Telescoped Route to 2,6-Disubstituted 2,3,4,5-Tetrahydropyridines and 2,6-syn-Disubstituted Piperidines: Total Synthesis of (-)-Grandisine G [J].

Cuthbertson, James D. ;

Taylor, Richard J. K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1490-1493

[8] Sulfoxide-directed enantioselective synthesis of functionalized dihydropyrans [J].

de la Pradilla, RF ;

Tortosa, M .

ORGANIC LETTERS, 2004, 6 (13) :2157-2160

[9] Targeted drugs by olefin metathesis: piperidine-based iminosugars [J].

Dragutan, Ileana ;

Dragutan, Valerian ;

Demonceau, Albert .

RSC ADVANCES, 2012, 2 (03) :719-736

[10] Sulfur-directed enantioselective synthesis of functionalized dihydropyrans [J].

Fernandez de la Pradilla, Roberto ;

Tortosa, Mariola ;

Lwoff, Nadia ;

del Aguila, Miguel A. ;

Viso, Alma .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6716-6727

← 1 2 3 4 5 →