synthesis 17/2011 - Thieme Chemistry

SYNTHESIS
2685 T. Lehnert
G. Özüduru
H. Grugel
F. Albrecht
S. M. Telligmann
M. M. K. Boysen*
2709 I. Wilkening
G. del Signore
W. Ahlbrecht
C. P. R. Hackenberger*
Journal of 2011
Synthetic Organic No. 17
Chemistry September I
More Than Just Sweet – Sugar-Derived Stereodifferentiating Agents for
Asymmetric Synthesis
chiral auxiliary chiral reagent chiral ligand chiral organocatalyst
Me
PivO
PivO
OPiv
O
OPiv
N
Me
R 1
O
Me
O
O
O
O O
Me
Cl
Ti
O
O
O
O
Me Me
O
Me
O
Me
Ph
O
O
O
Ar1 2P
O
O
Ar1 2P
OPh
O
Me Me
O
O
O
Me Me
Lewis Acid or Alkyl Halide Promoted Rearrangements of Phosphor- and
Phosphinimidates to N,N-Disubstituted Phosphor- and Phosphinamidates
R 1 N 3
R 1 = alkyl, Ph
P(OR2 )3
or
Ph2POR 2
acid Lewis
or
R 1 X
R 1
O
N P R3 R3 R 2
R3 Ph, O-alkyl
=
R2 alkyl =
NaN3 1.
P(OMe) 3
2.
3. BF3⋅OEt2
one-pot
R 1 X
R1 alkyl =
= Br X
2721 D. R. Romer Convenient Laboratory Method for the Synthesis of Symmetrical
1,3-Diphenylacetone Derivatives
Ph
O
OEt
NaH
toluene
Ph
O
CO2Et
Ph
AcOH
H2O HCl,
reflux
OMs
OTs
Ph
O
Ph
O
O
Review
Feature Article
PSP

Special Topics
VI Table of Contents
2724 P. van Delft
E. van Schie
N. J. Meeuwenoord
H. S. Overkleeft
G. A. van der Marel*
D. V. Filippov*
2733 M. Walter
T. Kottke
L. Weizel
J. S. Schwed
H. Stark*
2737 J. M. Aizpurua*
M. Sagartzazu-Aizpurua
I. Azcune
J. I. Miranda
Z. Monasterio
E. García-Lecina
R. M. Fratila
2743 Q. Zang
S. Javed
F. Ullah
A. Zhou
C. A. Knudtson
D. Bi
F. Z. Basha
M. G. Organ*
P. R. Hanson*
Oligonucleotide Conjugates by Means of Copper-Free Click Chemistry –
Expanding the Repertoire of Strained Cyclooctyne Phosphoramidites
DMTO
O
HN
O
O
P
N
O
O
N
3' dT modifier
oligonucleic acid
N
H
O
O
N
N N
O N
P
3
O
fluorescent label
S
S
3
N
H
O
O
CN
modifier with a cleavable linker
5'
Synthesis of 1,2,3-Triazole Elements in Histamine H 3 Receptor Ligands
N O
R
+
N 3
CuSO4
sodium ascorbate
DMF–H2O
N O
hH3R Ki 9–430 nM
‘Click’ Synthesis of Nonsymmetrical 4,4¢-Bis(1,2,3-triazolium) Salts
R 1
N
N N
1) (R 3 O) 3OBF 4
N3R 2) 2
cat. Cu(I)
R 1
N
N +
N
R 3
N N
N R2
BF4 –
R1 alkyl, aryl
=
R2 alkyl, aryl, peptidyl, glycosyl
=
R 3 , R 4 = Me, Et, allyl
(R 4 O)3OBF4
R 1
N
N
N N
N +
+
R 3
R 4
N R2
– BF4 2
R
N
N
N
R = CH2OH,
COOH,
COOMe
Application of a Double Aza-Michael Reaction in a ‘Click, Click, Cy-Click’
Strategy: From Bench to Flow
Cl
1. "click"
O O
S
Cl
TBSO
2. "click" RBr
NH 2
CO2Me
MACOS cy-"click"
3.
scale out
and
R 1 NH2
μW
O O
S
N
CO 2Me
4. "click"
N3
cyclize 3.
one-pot double aza-Michael
sequential
and Huisgen cycloaddition
R 2
O O
R2 S
N
R1 N
R 2
N
O
S
N
R1 CO 2Me
O
N
N
N
CO 2Me

Table of Contents VII
2751 D. Shpasser
M. Kapon
M. Botoshansky
M. S. Eisen*
2754 M. Hinoshita
D. Shibata
M. Hatakenaka
E. Okada*
2761 Z. Song
X.-P. He
G.-R. Chen*
J. Xie*
2767 H. Xie
J. Zhu
Z. Chen
S. Li
Y. Wu*
Triple Mukaiyama–Michael Cascade toward a Tricyclic Framework
TMSO
O
O
OTMS
+
O
1. ZnI 2
2. HF
O
O
HO
O
OTMS
Facile and Convenient Syntheses of Fluorine-Containing Pyrido[2,3-h]quinazolines
and 1,7-Phenanthrolines by Condensation Reactions of
6,8-Bis(trifluoroacetyl)quinolin-5-amine with Carbonyl Compounds
N
N
R 1 R 2
N
C(OH)2CF3
CF 3
R1CHO NH3
(as a nucleophile)
N
NH 2
COCF3
COCF3
new fluorine-containing
a
block
building
R 2 COCH 2R 3
NH3
a base)
(as
N
N
R 3
C(OH)2CF3
6-O-Amino-2-O-carboxymethyl Glucopyranoside as Novel Glycoaminoxy
Acid Building Block for the Construction of Oligosaccharide Mimetics
PG 2 O2C
glycoaminoxy acid
new
block
building
O
O
BnO OBn
MeO
BnO OBn
t-BuO2C O
MeO
O
ONPG 1
O
O NH
PG 1 = Phth; PG 2 = t-Bu
O
BnO OBn
MeO
O
to
assembly
oligosaccharide
novel
mimetics
O
O NH
n
O
BnO OBn
MeO
O
ONPhth
Reaction of a Trifluoromethylated N-Monosubstituted Hydrazone with
a,b-Ethenyl Ketones: A Novel Synthesis of Substituted Pyrazolidines and
Pyrazolines
F3C N NH
Ar 2
+
Ar 1
O
Ph
N
Ar
NH
1
(20 mol%) 8 examples
TfOH
toluene, r.t., 48 h
(10 mol%)
Cu(OTf)2
(20 mol%)
TfOH
air, toluene, 60 °C
Ar 1
Ar 2
Ar 2
O
O
Ph
CF 3
Ph
N
N
CF 3
to 91:9 dr
77:23
yield
65–86%
examples
17
to 92:8 dr
77:23
46–91% yield
CF 3
Short Paper
Papers

Papers
VIII Table of Contents
2775 T. W. T. Muesmann
M. S. Wickleder
J. Christoffers*
2781 V. Toum
C. Kadouri-Puchot*
L. Hamon
G. Lhommet
V. Mouriès-Mansuy
C. Vanucci-Bacqué
L. Dechoux*
2789 J.-S. Tang*
Y.-X. Xie
Z.-Q. Wang
J.-H. Li*
2796 D.-Y. Zhang
D.-S. Wang
M.-C. Wang*
C.-B. Yu
K. Gao
Y.-G. Zhou*
Preparation of Linear Aromatic Disulfonic Acids: New Linker Molecules for
Metal-Organic Frameworks
HO3S SO3H
HO3S SO3H
HO 3S SO 3H HO 3S SO 3H
N-Bromosuccinimide-Promoted Cyclization of b-Carboxymethyl Enamino
Esters; Synthesis of Functionalized 4-Amino-2(5H)-Furanones
MeO 2C
HN
CO2Me
R1 Ph
NBS, EtOAc
MeO2C 1) alkylation
O
decarboxylation
2)
HN
Bn
O
(H)Br
O
CO2Me
HN
R 1 Ph
R 2
HN
Br(H)
Efficient Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of
Iodoethynes with Arylboronic Acids under Aerobic Conditions
Pd(OAc) 2, Cs2CO3 I +
Ar
R 2 ArB(OH) R
R = amide, ester, Ph, n-C 5H 11
MeOH, r.t.
Bn
Synthesis of Electronically Deficient Atropisomeric Bisphosphine Ligands
and Their Application in Asymmetric Hydrogenation of Quinolines
R
I2, THF
[Ir(cod)Cl]2, ligand, 1 R1 R N 2 H2 (700 psi), r.t., 22 h
N
H
O
O
O
up to 95%
ee:
up to 14600
TON:
R 2
TfO
TfO
ligand
PPh 2
PPh 2

Table of Contents IX
2803 Y. Xie
M. Yu
Y. Zhang*
2810 D. Zheng
Z. Wang*
J. Wu*
2817 M. Hernández-Rodríguez*
T. Castillo-Hernández
K. E. Trejo-Huizar
2822 P. Perdih
J. Baškovč
G. Dahmann
U. Grošelj
D. Kočar
A. Novak
B. Stanovnik
J. Svete*
Iron(II) Chloride Catalyzed Alkylation of Propargyl Ethers: Direct
Functionalization of an sp 3 C–H Bond Adjacent to Oxygen
Ar
O O
R2 O
R1 O
H
O
R2 (20 mol%)
FeCl2
DDQ
O R1
Ar
35–57%
35–64%
H
3 FeCl
DDQ
R 1 = Me
Silver Triflate Catalyzed Reaction of 2-Alkynylbenzaldoxime with Phenol:
A General and Facile Route to 1-Aroxyisoquinolines
R 1
N OH
R 2
+
Ar OH
(10 mol%)
AgOTf
(2.0 equiv)
PyBroP
(3.0 equiv)
i-Pr2NEt
1,4-dioxane
R 1
Ar
MeO
O Ar
Asymmetric Synthesis of 1-(9-Anthracenyl)ethylamine and Its Trifluoromethyl
Analogue via Nucleophilic Addition to an N-(tert-Butylsulfinyl)imine
NH 2
3
Ar CH
(S)
Ar =
HN
O
S t-Bu
3
Ar CH
(S,RS)
H3CMgI LiCH3
Ar
N
O
S t-Bu
H
TMSCF 3
HN
O
S t-Bu
3
Ar CH
S) (R,R
HN
O
CF3
Ar
(S,RS)
S t-Bu
N
R 2
Ar
H
O
Ar
Ar
NH 2
3 CH
(R)
Parallel Synthesis of 1-Substituted 5-(5-Oxopyrrolidin-3-yl)-1H-pyrazole-4carboxamides
HOOC
COOH
Ph
R 1
5 steps R 2 R 3 NH
N
N
N
COOH
R 1 = Me, Ph
O
R 1
N
N
Ph
N
O
O
NR 2 R 3
24-compound library
NH 2
(S)
CF 3
Papers

Papers
X Table of Contents
2833 O. Vakuliuk
B. Koszarna
D. T. Gryko*
2838 P. B. Wakchaure
N. P. Argade*
2843 K. V. Belyaeva
L. V. Andriyankova
L. P. Nikitina
A. V. Ivanov
A. V. Afonin
I. A. Ushakov
A. G. Mal’kina
A. I. Mikhaleva
B. A. Trofimov*
2848 N. Tolle
U. Dunkel
L. Oehninger
I. Ott
L. Preu
T. Haase
S. Behrends
P. G. Jones
F. Totzke
C. Schächtele
M. H. G. Kubbutat
C. Kunick*
Direct Arylation of Pyrrole Derivatives in Superbasic Media
+
N
145 °C, overnight
N
R 26–86%
2
R 1
I
LiOH, DMSO
Intramolecular Chemoselective Acylation of a Suitably Substituted
Isoindole: Synthesis of (±)-Chilenine and (±)-Deoxychilenine
MeO
OMe
O
O
O
3,4-dimethoxyhomophthalic
anhydride
5 steps
O
O
O
R
R 1
N
O
(R = OH) 64%
chilenine
(R = H) 62%
deoxychilenine
Synthesis of 1-Vinylpyrrole-imidazole Alkaloids
N
N
Me
Ph
+ +
CN
R 2
R 1
N
O
MeCN
24–72 h
r.t.,
N
N
Me
N
OMe
OMe
CN
R 2
R 2 R1
Ph
O
Ph
CN
up to 45%
Synthesis and Structure of Fluorescent Chelate Boron Complexes of
4-Anilinomethylidene-1-benzazepine-2,5-dione Ligands

Table of Contents XI
2859 R. Duddu*
M.-X. Zhang
R. Damavarapu*
N. Gelber
Molten-State Nitration of Substituted Imidazoles: New Synthetic Approaches
to the Novel Melt-Cast Energetic Material, 1-Methyl-2,4,5-trinitroimidazole
N
N
Me
NO2X
X = OTf, BF4
XIII Forthcoming Articles
O 2N
N
O2N NO2 N
Me
MTNI
NO 2BF 4
HNO 3–H 2SO 4
or
O 2N
N
N
Me
NO2
Papers

XII Table of Contents
Author Index
Afonin, A. V. 2843
Ahlbrecht, W. 2709
Aizpurua, J. M. 2737
Albrecht, F. 2685
Andriyankova, L. V. 2843
Argade, N. P. 2838
Azcune, I. 2737
Baškovč, J. 2822
Basha, F. Z. 2743
Behrends, S. 2848
Belyaeva, K. V. 2843
Bi, D. 2743
Botoshansky, M. 2751
Boysen, M. M. K. 2685
Castillo-Hernández, T. 2817
Chen, G.-R. 2761
Chen, Z. 2767
Christoffers, J. 2775
Dahmann, G. 2822
Damavarapu, R. 2859
Dechouz, L. 2781
del Signore, G. 2709
Duddu, R. 2859
Dunkel, U. 2848
Eisen, M. S. 2751
Filippov, D. V. 2724
Fratila, R. M. 2737
Gao, K. 2796
García-Lecina, E. 2737
Gelber, N. 2859
Grošelj, U. 2822
Grugel, H. 2685
Gryko, D. T. 2833
Haase, T. 2848
Hackenberger, C. P. R. 2709
Hamon, L. 2781
Hanson, P. R. 2743
Hatakenaka, M. 2754
He, X.-P. 2761
Hernández-Rodríguez, M. 2817
Hinoshita, M. 2754
Ivanov, A. V. 2843
Javed, S. 2743
Jones, P. G. 2848
Kadouri-Puchot, C. 2781
Kapon, M. 2751
Knudtson, C. A. 2743
Kočar, D. 2822
Koszarna, B. 2833
Kottke, T. 2733
Kubbutat, M. H. G. 2848
Kunick, C. 2848
Lehnert, T. 2685
Lhommet, G. 2781
Li, J.-H. 2789
Li, S. 2767
Mal’kina, A. G. 2843
Meeuwenoord, N. J. 2724
Mikhaleva, A. I. 2843
Miranda, J. I. 2737
Monasterio, Z. 2737
Mouriès-Mansuy, V. 2781
Muesmann, T. W. T. 2775
Nikitina, L. P. 2843
Novak, A. 2822
Oehninger, L. 2848
Okada, E. 2754
Organ, M. G. 2743
Ott, I. 2848
Overkleeft, H. S. 2724
Özüduru, G. 2685
Perdih, P. 2822
Preu, L. 2848
Romer, D. R. 2721
Sagartzazu-Aizpurua, M. 2737
Schächtele, C. 2848
Schwed, J. S. 2733
Shibata, D. 2754
Shpasser, D. 2751
Song, Z. 2761
Stanovnik, B. 2822
Stark, H. 2733
Svete, J. 2822
Tang, J.-S. 2789
Telligmann, S. M. 2685
Tolle, N. 2848
Totzke, F. 2848
Toum, V. 2781
Trejo-Huizar, K. E. 2817
Trofimov, B. A. 2843
Ullah, F. 2743
Ushakov, I. A. 2843
Vakuliuk, O. 2833
van Delft, P. 2724
van der Marel, G. A. 2724
van Schie, E. 2724
Vanucci-Bacqué, C. 2781
Wakchaure, P. B. 2838
Walter, M. 2733
Wang, D.-S. 2796
Wang, M.-C. 2796
Wang, Z. 2810
Wang, Z.-Q. 2789
Weizel, L. 2733
Wickleder, M. S. 2775
Wilkening, I. 2709
Wu, J. 2810
Wu, Y. 2767
Xie, H. 2767
Xie, J. 2761
Xie, Y. 2803
Xie, Y.-X. 2789
Yu, C.-B. 2796
Yu, M. 2803
Zang, Q. 2743
Zhang, D.-Y. 2796
Zhang, M.-X. 2859
Zhang, Y. 2803
Zheng, D. 2810
Zhou, A. 2743
Zhou, Y.-G. 2796
Zhu, J. 2767