Styrylmalonates as an Alternative to Donor-Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones

被引：29

作者：

Borisov, Denis D. ^{[1
]}

Novikov, Roman A. ^{[1
,2
]}

Eltysheva, Anna S. ^{[1
]}

Tkachev, Yaroslav V. ^{[2
]}

Tomiloy, Yury V. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

[2] Russian Acad Sci, Engelhardt Inst Mol Biol, 32 Vavilov St, Moscow 119991, Russia

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 14期

基金：

俄罗斯科学基金会;

关键词：

AROMATIC-ALDEHYDES; DERIVATIVES; CYCLOADDITION; NITROSOARENES; CONSTRUCTION; ANNULATION; MECHANISM;

D O I：

10.1021/acs.orglett.7b01556

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy for modifying the reactivity of donor-acceptor cyclopropanes (DAC) has been suggested. It involves the use of isomeric styrylmalonates as alternative sources of reactive intermediates. The efficiency of the approach has been demonstrated in reactions with aromatic aldehydes. As a result, a new process for Construction of the 5,6-dihydropyran-2-one skeleton has been developed. It efficiently occurs with high diastereoselectivity in the presence of BF3.Et(2)Q; the products can be easily isolated by crystallization. The subsequent use of the resulting dihydropyranones in syntheses providing convenient access to various classes of compounds with broad molecular diversity has been demonstrated.

引用

页码：3731 / 3734

页数：4

共 33 条

[1] GaCl3-Mediated Reactions of Donor-Acceptor Cyclopropanes with Aromatic Aldehydes [J].

Borisov, Denis D. ;

Novikov, Roman A. ;

Tomilov, Yury V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) :12233-12237

[2] [3+2] Cyclodimerization of 2-arylcyclopropane-1,1-diesters. Lewis acid induced reversion of cyclopropane umpolung [J].

Chagarovskiy, Alexey O. ;

Ivanova, Olga A. ;

Budynina, Ekaterina M. ;

Trushkov, Igor V. ;

Melnikov, Mikhail Ya .

TETRAHEDRON LETTERS, 2011, 52 (34) :4421-4425

[3] Lewis Acid-Catalyzed Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates: A New Efficient Route to 2-Styrylmalonates [J].

Chagarovskiy, Alexey O. ;

Ivanova, Olga A. ;

Rakhmankulov, Eduard R. ;

Budynina, Ekaterina M. ;

Trushkov, Igor V. ;

Melnikov, Mikhail Ya. .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) :3179-3184

[4] Cascade Reaction of Donor-Acceptor Cyclopropanes: Mechanistic Studies on Cycloadditions with Nitrosoarenes and cis-Diazenes [J].

Chidley, Tristan ;

Vemula, Naresh ;

Carson, Cheryl A. ;

Kerr, Michael A. ;

Pagenkopf, Brian L. .

ORGANIC LETTERS, 2016, 18 (12) :2922-2925

[5] Enantioselective Total Synthesis of (-)-Pironetin: Iterative Aldol Reactions of Thiazolidinethiones [J].

Crimmins, Michael T. ;

Dechert, Anne-Marie R. .

ORGANIC LETTERS, 2009, 11 (07) :1635-1638

[6] Tetrahydroquinolines via Stereospecific [3+3]-Annulation of Donor-Acceptor Cyclopropanes with Nitrosoarenes [J].

Das, Saikat ;

Chakrabarty, Shyamal ;

Daniliuc, Constantin G. ;

Studer, Armido .

ORGANIC LETTERS, 2016, 18 (11) :2784-2787

[7] Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes [J].

de Nanteuil, F. ;

De Simone, F. ;

Frei, R. ;

Benfatti, F. ;

Serrano, E. ;

Waser, J. .

CHEMICAL COMMUNICATIONS, 2014, 50 (75) :10912-10928

[8] Lewis Acid Catalyzed Diastereoselective Cycloaddition Reactions of Donor Acceptor Cyclopropanes and Vinyl Azides: Synthesis of Functionalized Azidocyclopentane and Tetrahydropyridine Derivatives [J].

Dey, Raghunath ;

Banerjee, Prabal .

ORGANIC LETTERS, 2017, 19 (02) :304-307

[9] [4+3] Cycloaddition of Donor-Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho-Bisthioquinone [J].

Garve, Lennart K. B. ;

Pawliczek, Martin ;

Wallbaum, Jan ;

Jones, Peter G. ;

Werz, Daniel B. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (02) :521-525

[10] Carbocycles from donor-acceptor cyclopropanes [J].

Grover, Huck K. ;

Emmett, Michael R. ;

Kerr, Michael A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) :655-671

← 1 2 3 4 →