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Tetrahedron Vol. 69, Issue 37, 2013 Contents REPORT Development and applications of highly selective palladium-catalyzed monocoupling reactions of (cyclo)alkenes and 1,3-alkadienes bearing two or three electrophilic sites and bis(enol triates) with terminal alkynes pp 7869e7909 Renzo Rossi*, Fabio Bellina* Marco Lessi, Chiara Manzini ARTICLES Aryl N-methyliminodiacetic acid (MIDA) boronates from cyclotrimerization of ethynyl MIDA boronate with diynes pp 7910e7915 Silje Melnes, Annette Bayer, Odd R. Gautun* R B O O O O N B O O O O N B O O O O N + R + R M-cat Contents lists available at SciVerse ScienceDirect Tetrahedron journal homepage: www.elsevier.com/locate/tet Tetrahedron 69 (2013) 7861e7868
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Page 1: Graphical contents list

Tetrahedron 69 (2013) 7861e7868

Contents lists available at SciVerse ScienceDirect

Tetrahedron

journal homepage: www.elsevier .com/locate/ tet

Tetrahedron Vol. 69, Issue 37, 2013

Contents

REPORT

Development and applications of highly selective palladium-catalyzed monocoupling reactions of (cyclo)alkenes and1,3-alkadienes bearing two or three electrophilic sites and bis(enol triflates) with terminal alkynes

pp 7869e7909

Renzo Rossi*, Fabio Bellina* Marco Lessi, Chiara Manzini

ARTICLES

Aryl N-methyliminodiacetic acid (MIDA) boronates from cyclotrimerization of ethynyl MIDA boronate with diynes

pp 7910e7915 Silje Melnes, Annette Bayer, Odd R. Gautun*

RB OO O

O

N BOO

O

ON

B

O O

O

O

N+

R

+

R

M-cat

Page 2: Graphical contents list

Contents / Tetrahedron 69 (2013) 7861e78687862

One-pot synthesis of functionalized p-terphenyl derivatives pp 7916e7924

Meng-Yang Chang*, Chieh-Kai Chan, Ming-Hao Wu

2c

3b+

aldol

condensation

electrocyclization /

oxidative dehydrogenation

1h (80%)X-Ray

NaH

THF

CHO

S

O

O

S

O

O

F

F

Ligand-free indium(III)-catalyzed Heck reaction pp 7925e7930

Pei Liu, Ying-ming Pan*, Kun Hu, Xiao-chao Huang, Ying Liang, Heng-shan Wang*

R + IR' R' R

Pd-free

Ligand-free

DMF, 140 oC, 24 h 21 examples

Isolated yields:75-96%

CH3COONa

InCl3

A new route toward 2-acetamido-4-O-methyl-2-deoxy-D-mannopyranose from a Ferrier derivative of pp 7931e7935

tri-O-acetyl-D-glucal, which contributes to aldolase-catalyzed synthesis of laninamivir (CS-8958) Hayato Okazaki, Kengo Hanaya, Mitsuru Shoji, Noriyasu Hada, Takeshi Sugai*

One-pot synthesis of 2-sulfanyl-3-sulfinyl(or sulfonyl)-1H-indoles via cyclization of 1-isothiocyanato-2- pp 7936e7942

[sulfinyl(or sulfonyl)methyl]benzenes with sodium hydride Kazuhiro Kobayashi*, Akihiro Kobayashi, Kosuke Ezaki
Page 3: Graphical contents list

Contents / Tetrahedron 69 (2013) 7861e7868 7863

Synthesis and properties of porphyrin-expanded porphyrin click dyads pp 7943e7949

Yogita Pareek, Mangalampalli Ravikanth*

Six covalently linked triazole bridged porphyrin-expanded porphyrin dyads containing Zn(II) porphyrin as energy donor and thiarubyrin, oxasmar-agdyrin and BF2eoxasmaragdyrin as energy acceptors were synthesized under click reaction conditions and studied their absorption, electrochemicaland photophysical properties.

Role of the electron-donating methoxy group on the photo-induced cyclization of 2-azadienes: a mechanistic study pp 7950e7955

Pedro J. Campos, Míriam Caro, Miguel A. Rodríguez*

Intramolecular DielseAlder route to angularly oxygenated hydrindanes. Synthesis of the functionalized bicylic skeleton pp 7956e7963

present in galiellalactone Md. Firoj Hossain, Ram Naresh Yadav, Sujit Mondal, Anupam Jana, Subrata Ghosh*

Astins KeP, six new chlorinated cyclopentapeptides from Aster tataricus pp 7964e7969

Hui-Min Xu, Guang-Zhi Zeng, Wen-Bing Zhou, Wen-Jun He, Ning-Hua Tan*
Page 4: Graphical contents list

Contents / Tetrahedron 69 (2013) 7861e78687864

a-Regioselective construction of gem-bisprenyl structures via zinc-mediated prenylation of esters in THF pp 7970e7974

Li-Ming Zhao*, Li-Jing Wan, Shu-Qing Zhang, Rui Sun, Feng-Yan Ma

R

HOR

O

OR'

Br

Zn/THF/reflux

The in situ generated prenylzinc reagent has been shown to undergo a new type of a-regioselective addition reactionwith awide range of esters thataffords gem-bisprenyl structures.

Reactions of 2-(trifluoromethyl)-2-hydroxy-2H-chromenes with silyl enol ethers promoted by AlCl3 pp 7975e7980

Liang Zhang, Xinjin Li, Zhongwei Wang*, Jingwei Zhao*, Jinjin Wang, Jianwei Han, Shizheng Zhu*

A reversible fluorescent chemosensor for mercury ions based on 1H-imidazo[4,5-b]phenazine derivatives pp 7981e7987

BingBing Shi, Peng Zhang, TaiBao Wei, Hong Yao, Qi Lin, Jun Liu, YouMing Zhang*

In(OTf)3 catalyzed N-benzylation of amines utilizing benzyl alcohols in water pp 7988e7994

Jin-Ming Yang, Ran Jiang, Lin Wu, Xiao-Ping Xu, Shun-Yi Wang, Shun-Jun Ji*
Page 5: Graphical contents list

Contents / Tetrahedron 69 (2013) 7861e7868 7865

BayliseHillman carbonates in organic synthesis: a convenient one-pot strategy for nitroneespiro-oxindole frameworks pp 7995e8001

Deevi Basavaiah*, Satpal Singh Badsara, Gorre Veeraraghavaiah

N

N

R2

ON

OBocO

R2

O

1. DMAP, DCMrt, 12 h, N2

2. Fe/HCl, C2H5OHrt, 12 h

R1

R3

R3

+

O

R1

R3

R3

R1 = H, Cl, Br ; R2 = Me, Et, BnR3 = H, Me 56-65%

2a-l4a-l

MeNO2

Gold(I) catalysed cycloisomerisation of b-hydroxy propargylic esters to dihydropyrans/2H-pyrans via allene pp 8002e8012

intermediates Ramesh Kotikalapudi, K.C. Kumara Swamy*

R OH

O

O

R O

O

O

H

R O

O

O

H

R1

R2

R3

R2

R3

R1

2 mol% Ph3PAuCl/

AgSbF6

CH2Cl

2, rt R

2

R3

R1

or

via Allene Intermediate

Diversity oriented catalyst-free and solvent-free one-potMCR at room temperature: rapid and regioselective convergent pp 8013e8018

approach to highly functionalized dihydro-4H-thiopyrans Suvajit Koley, Sushobhan Chowdhury, Tanmoy Chanda, B. Janaki Ramulu, Maya Shankar Singh*

Synthesis and antitumor activity of des-AB analogue of steroidal saponin OSW-1 pp 8019e8024

Daishiro Minato, Bozhi Li, Dejun Zhou, Yasumi Shigeta, Naoki Toyooka, Hiroaki Sakurai, Kenji Sugimoto,Hideo Nemoto, Yuji Matsuya*
Page 6: Graphical contents list

Contents / Tetrahedron 69 (2013) 7861e78687866

Synthesis of indole-2-, 3-, or 5-substituted propargylamines via gold(III)-catalyzed three component reaction of pp 8025e8033

aldehyde, alkyne, and amine in aqueous medium Venu Srinivas, Mamoru Koketsu*

5

2

Synthesis of the first conjugates of 5-ethynyl-20-deoxyuridine with closo-dodecaborate and cobalt-bis-dicarbollide pp 8034e8041

boron clusters Andrey Semioshkin*, Anna Ilinova, Irina Lobanova, Vladimir Bregadze, Edyta Paradowska, Miros1awa Studzi�nska,Agnieszka Jab1o�nska, Zbigniew J. Lesnikowski

N

O

O

N

NH

O

O

O

O

HO

B

O+

X

Si

Si

X

N+

O

O

N

NH

O

O

HO

OH

O

B

boron

clusterboron

cluster

Model support studies toward the total synthesis of the stemona alkaloid stemocurtisine pp 8042e8050

Sudhir R. Shengule, Anthony C. Willis, Stephen G. Pyne*

Experimental and computational study of the complexation of adamantyl glycosides with b-cyclodextrin pp 8051e8063

�Zeljka Car, Ivan Kodrin, Josip Po�zar, Rosana Ribi�c, Davor Kova�cevi�c, Vesna Petrovi�c Perokovi�c*
Page 7: Graphical contents list

Contents / Tetrahedron 69 (2013) 7861e7868 7867

Synthesis of a novel diene from a cyclobutane precursor: an entry to 2,9-disubstituted [2]diadamantanes pp 8064e8068

Savvas Ioannou, Harry Krassos, Athanassios V. Nicolaides*

A new strategy for facile synthesis of tetrasubstituted pyridine derivatives pp 8069e8073

Jun Chen, Hangcheng Ni, Wenteng Chen, Guolin Zhang*, Yongping Yu*

Structure and stereochemistry of an anti-inflammatory anhydrosugar from the Australianmarine sponge Plakinastrella pp 8074e8079

clathrata and the synthesis of two analogues Peter L. Katavic, Ken W.L. Yong, Joel N. Herring, Myrna A. Deseo, Joanne T. Blanchfield, Vito Ferro, Mary J. Garson*

The structure, relative and absolute configuration of a glycolipid component 1 isolated from Plakinastrella clathrata have been confirmed by synthesis

of analogues 3 and 4.

Epoxysilanes as substrates in regio- and stereo-specific synthesis of silylated g-hydroxyphosphane oxides, precursors of pp 8080e8087

stereodefined allylphosphane oxides Ana M. Gonz�alez-Nogal*, Purificaci�on Cuadrado

O SiR SiR

R PPh

O

R

HO

R

PPh

OSiRPh P

O

OH

Ph P

O

OSiR

R

RR

R α-cleavageβ-cleavage

R PPh

O

Page 8: Graphical contents list

Contents / Tetrahedron 69 (2013) 7861e78687868

The dual role of ionic liquid BmimBF4, precursor of N-heterocyclic carbene and solvent, in the oxidative esterification pp 8088e8095

of aldehydes Isabella Chiarotto*, Marta Feroci, Giovanni Sotgiu, Achille Inesi*

*Corresponding authorSupplementary data available via ScienceDirect

Available online at www.sciencedirect.com

ScienceDirect

Full text of this journal is available, on-line from ScienceDirect. Visitwww.sciencedirect.com for more information.

Abstracted/indexed in: AGRICOLA, Beilstein, BIOSIS Previews, CAB Abstracts, Chemical Abstracts. Current Contents: Life Sciences,Current Contents: Physical, Chemical and Earth Sciences, Current Contents Search, Derwent Drug File, Ei compendex, EMBASE/Excerpta Medica, PASCAL, Research Alert, Science Citation Index, SciSearch. Also covered in the abstract and citation databaseSCOPUS�. Full text available on ScienceDirect�

ISSN 0040-4020


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