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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 AsensioNewmannose-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. BajajSynthesis of polysubstituted 3H-pyrimidin-4-ones from cyanoacetamides under Vilsmeier conditions pp 7081e7084
Zhiguo Zhang, Can Xue, Xiao Liu, Qian Zhang*, Qun LiuCyclopeptides 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 Cu2DRosa 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 GuillaumetManganese(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 RiedeN 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�eroˇ
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. AlvesContents / 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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