Tetrahedron 67 (2011) 6961e6967

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Tetrahedron

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

Tetrahedron Vol. 67, Issue 37, 2011

Contents

REPORT

Highly selective palladium-catalyzed SuzukieMiyauramonocoupling reactions of ethene and arene derivatives bearingtwo or more electrophilic sites

pp 6969e7025

Renzo Rossi*, Fabio Bellina* Marco Lessi

Selective SuzukieMiyaura monocoupling reactions of di- and polyhalogenated ethenes and di- and polyhalogenated arene derivatives bearing different or iden-tical halogen atoms are reviewed, and the reasons for the observed stereo-, site- and/or chemo-selectivities are discussed. The use of these reactions as key steps in

the synthesis of naturally-occurring compounds, bioactive substances including drugs and liquid crystals is also reported.

ARTICLES

Synthesis and ‘click’ cycloaddition reactions of tetramethoxy- and tetrapropoxy-2-(u-azidoalkyl)calix[4]arenes

pp 7027e7034 Michael J. Hardman, Ashley M. Thomas, Louise T. Carroll, Linus C. Williams, Sean Parkin, Jordan L. Fantini*

Contents / Tetrahedron 67 (2011) 6961e69676962

Asymmetric synthesis of diverse a,a-diarylmethylamines via aryl Grignard additions to chiral N-2,4,6-triisopropylbenzenesulfinylimines

pp 7035e7041

Zhengxu Han*, Robert Busch, Keith R. Fandrick, Angelica Meyer, Yibo Xu, Dhileep K. Krishnamurthy, Chris H. Senanayake

NSO

NH

SO

MgX

toluene, r.t.

19 examples, upto >95:5 d.r.

R1

R2

R1

R2

R1 = H, Cl, F, CF3, MeO R2= Me2N, H, MeO, Cl

Amino acids as building blocks for the synthesis of substituted 1,2,4-triazoles pp 7042e7049

Mathieu Bibian, Jean Martinez, Jean-Alain Fehrentz*

PHN∗

X

N N

N

∗P'O2C Y

∗

NHP''

ZPHN

∗ HN

S

∗ CO2P'

Y

X+ H2NHN ∗

ONHP''

Z

optically pure compoundsX, Y, Z are amino acid side chainsP, P', P'' are protecting group

The role of Zn2D in enhancing the rate and stereoselectivity of the aldol reactions catalyzed by the simple prolinamide pp 7050e7056

model Cecilia Andreu*, Gregorio Asensio

Newmannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. pp 7057e7065

Part 3: Chiral ketones from sugars Jos�e M. Vega-P�erez*, Ignacio Peri~n�an, Margarita Vega-Holm, Carlos Palo-Nieto, Fernando Iglesias-Guerra*

Contents / Tetrahedron 67 (2011) 6961e6967 6963

Synthesis of macrotetrolide a, a designed polynactin analog composed of bishomononactic acids

pp 7066e7072 Kentaro Takai, Tadaatsu Hanadate, Masaki Abe, Yukie Ono, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota*

(+)(–)O

O

O O

O O

O

O

OOO

O

(+) (–)

macrotetrolide α

BnOO

O Oiodoetherificationoptical resolution

macrolactonization

Enantioselective O-acetylcyanation/cyanoformylation of aldehydes using catalysts with built-in crown ether-like motif pp 7073e7080

in chiral macrocyclic V(V) salen complexes Noor-ul H. Khan*, Arghya Sadhukhan, Nabin C. Maity, Rukhsana I. Kureshy, Sayed H.R. Abdi, S. Saravanan, Hari C. Bajaj

Synthesis of polysubstituted 3H-pyrimidin-4-ones from cyanoacetamides under Vilsmeier conditions pp 7081e7084

Zhiguo Zhang, Can Xue, Xiao Liu, Qian Zhang*, Qun Liu

Cyclopeptides and polyketides from coral-associated fungus, Aspergillus versicolor LCJ-5-4 pp 7085e7089

Yibin Zhuang, Xiancun Teng, Yi Wang, Peipei Liu, Hui Wang, Jing Li, Guoqiang Li, Weiming Zhu*

N

R NH

NHN

HN

O

O

O

O

O

Proa

Phea

Prob

Pheb

1: R = CH3; 2: R = H; 3: R = CH2OH

OHO O O OH

5

4

6

OO

OH

OH

O

OH

OH

O

Contents / Tetrahedron 67 (2011) 6961e69676964

A novel Friedlander-type synthesis of 3-aryl quinolines from 3-oxo-2,3-diaryl-propionaldehydes

pp 7090e7095 Wanrong Luo, Qiuchao Mu, Wenwei Qiu, Ting Liu, Fan Yang, Xiaofeng Liu*, Jie Tang*

An ‘offeon’ fluorescent chemosensor of selectivity to Cr3D and its application to MCF-7 cells pp 7096e7100

Zhanxian Li, Wanying Zhao, Yuna Zhang, Lifeng Zhang, Mingming Yu*, Jinxia Liu*, Hongyan Zhang*

L-Proline-catalysed three-component domino reactions for the diastereoselective synthesis of 5,6-disubstituted pp 7101e7105

3-thiomorpholinones Sethuraman Indumathi, Subbu Perumal*, J. Carlos Men�endez*

EtO2C SAr'

O+ ArCHO + NH3

L-Pro (50 mol%),

EtOH

NH

S

OAr

Ar'

O

Created bonds

Imidazo-benzo-15-crown-5 ethers bearing arylthienyl and bithienyl moieties pp 7106e7113

as novel fluorescent chemosensors for Pd2D and Cu2D

Rosa M.F. Batista, Elisabete Oliveira, Susana P.G. Costa, Carlos Lodeiro*, M. Manuela M. Raposo*

3 3 + Pd2+

Contents / Tetrahedron 67 (2011) 6961e6967 6965

Synthesis of nucleoside aminooxy acids

pp 7114e7120 Yanchun Gong, Sandrine Peyrat, Hongbin Sun, Juan Xie*

OAc

CO2H

OAc

O

O

NPhth

CO2H

OAc

O

O

NPhthBase = U, T, C

Bz, A

Bz, G

Ac,DPC

Base

O

OPhthN OAc

U

tBuO2CO

O OH

U

HNO

Nucleoside aminooxy acids

N-oxy amide-linked dinucleoside

Ammonia borane as a metal free reductant for ketones and aldehydes: a mechanistic study pp 7121e7127

Xianghua Yang, Thomas Fox, Heinz Berke*

H3N BH3

+O

R R'

THF +NH3

B OR

R' 3

RDS!

NH3

H3N BH

HO

RR'

Fast!H

O

R R'2

MeOH+

HO

R R'

B(OMe)3

NH3+

HH

Pd-catalyzed regiocontrolled Sonogashira and Suzuki cross-coupling reaction of 3,6-dihalogenoimidazo[1,2-a] pp 7128e7138

pyridines: one-pot double-coupling approach Ahmed El Akkaoui, Ibtissam Bassoude, Jamal Koubachi, Sabine Berteina-Raboin*, Abderrahim Mouaddib, G�erald Guillaumet

Manganese(III)-mediated oxidative annulation of vinylidenecyclopropanes with 1,3-dicarbonyl compounds pp 7139e7142

Wei Yuan, Yin Wei, Min Shi*

+OO

Ar2

Ar1 . Mn(OAc)3.2H2O (2.0 equiv)

CH3CN, HOAc (5.0 equiv), 60 oC, 6 h

3.0 equiv

OAr2

Ar1

O

31-92% yield

Manganese(III)-mediated oxidative annulation of vinylidenecyclopropanes with 1,3-dicarbonyl compounds in acetonitrile/acetic acid produces thecorresponding functionalized dihydrofuran derivatives in moderate to good yields under mild conditions. The substrate scope has been examinedand a plausible reaction mechanism has been also proposed on the basis of experimental results and previous literature.

Contents / Tetrahedron 67 (2011) 6961e69676966

Assessing chiral self-recognition using chiral stationary phases

pp 7143e7147 Wonjae Lee, Seth E. Snyder, Phillip I. Volkers, William H. Pirkle, David A. Engebretson, William A. Boulanger,Huei-Shian Lin, Bin-Syuan Huang, James R. Carey*

Synthesis of thiophene-substituted aza-BODIPYs and their optical and electrochemical properties pp 7148e7155

Roland Gresser, Horst Hartmann*, Marion Wrackmeyer, Karl Leo, Moritz Riede

N N

N

BFF

1a

N N

N

BFF

1b

S

N N

N

BFF

1c

N N

N

BFF

1d

S

S

S

S

S S

S S

S

Donor/acceptor-substituted anthradithiophene materials: synthesis, optical and electrochemical properties pp 7156e7161

Jean-Yves Balandier, Florence Quist, Noham Sebaihi, Claude Niebel, Benoît Tylleman, Pol Boudard, Saïd Bouzakraoui,Vincent Lemaur, J�ero

ˇ

me Cornil, Roberto Lazzaroni, Yves Henri Geerts, Sara Stas*

Highly diastereoselective synthesis of 2-azabicyclo[2.2.1]hept-5-ene derivatives: Bronsted acid catalyzed pp 7162e7172

aza-DielseAlder reaction between cyclopentadiene and imino-acetates with two chiral auxiliaries Xerardo García-Mera*, Jos�e E. Rodríguez-Borges*, M. Luísa C. Vale, Maria J. Alves

Contents / Tetrahedron 67 (2011) 6961e6967 6967

Photochromism of dihydroindolizines. Part 16: Tuning of the photophysical behavior of photochromicdihydroindolizines in solution and in polymeric thin film

pp 7173e7184

Saleh A. Ahmed*, Zeinab A. Hozien, Aboel-Magd A. Abdel-Wahab, Shaya Y. Al-Raqa, Abdulrahman A. Al-Simaree, Ziad Moussa,Saleh N. Al-Amri, Mouslim Messali, Ahmed S. Soliman, Heinz D€urr

*Corresponding authorSupplementary data available via ScienceDirect

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