synlett 09/2010

SYNLETT
1289 M. Zeng
S.-L. You*
1302 L. Kiss
F. Fülöp*
1315 D. J. Cox
T. B. Parsons
A. J. Fairbanks*
Accounts and 2010
Rapid Communications in No. 9
Synthetic Organic Chemistry June I
Asymmetric Friedel–Crafts Alkylation of Indoles: The Control of
Enantio- and Regioselectivity
Ar
N
N
H
Ts
H
R
H
alkylating reagents:
O
H
AFC
O
R 1 R 2
AFC = Asymmetric Friedel–Crafts alkylation
Ar
R
O
O
R
O
P
NO2
OH
, etc.
Selective Syntheses of Functionalized Cyclic b-Amino Acids via
Transformation of the Ring C–C Double Bonds
P 1 HN
( ) n
HO
( )n
COOR
NHP
HO
COOR
NHP
N3 COOR
( ) n
NHP
( ) n
O
NH
( ) n
N
)n P ( 2
COOR
NHP
O COOR
( )n
COOR
NHP
NHP
O
N
On the Hydrogenation of Glycosyl Oxazolines
HO
HO
OP(O)(ONa) 2
O
N O
H2, Pd
NaOMe
then
MeOH
= Ac (electron-withdrawing)
R
not cleaved
oxazoline
RO
RO
R 2
HO
HO
( )n
( )n
OP(O)(OBn)2
O
N O
COOR
NHP
R 1
H2, Pd
COOR
NHP
N
N
HO
N
HO
HO
( ) n
COOR
NHP
OP(O)(ONa)2
O
AcHN
H
H
= Bn (electron-donating)
R
reduction
oxazoline
Accounts
Letters

Letters
VI Table of Contents
1319 M. Catir
H. Kilic*
1323 J. A. Tamayo*
F. Franco
D. Lo Re
1327 A. Rahimi
A. Schmidt*
Benzylic and Allylic Oxidations with Bis(trifluoroacetoxyiodo)benzene and
tert-Butyl Hydroperoxide
I
•
t-BuOO
OOt-Bu
OOt-Bu
PhI
A Concise Synthesis of 6-Amino-6-deoxy-DNJ and 6-Amino-1,6-dideoxy-Ltalonojirimycin
OH
HO OH
N
H
NH 2
6-amino-1,6-dideoxy-
D-nojirimycin
O
O
O 2
4 steps
CMe
steps 6
HO
OH
OH
O
OH
HO OH
N
H
NH2
6-amino-1,6-dideoxy-
L-talonojirimycin
A Cyclobutene-1,2-Bis(imidazolium) Salt as Efficient Precursor of
Palladium-Catalyzed Room-Temperature Suzuki–Miyaura Reactions
Me
Me
N
N
N +
N +
Cl
Cl
2 BF 4 –
Cl
Cl
Pd(OAc)2
NaOt-Bu
toluene
r.t.
1331 P. Hudhomme* Selective C-tert-Butoxycarbonylation Using Di-tert-butyl Dicarbonate for the
Synthesis of Multifunctional Carbon Compounds
H
H
C CN N
2R CO 1
R
C
2
O
R1 Me, Ot-Bu
=
R2 Me, Ot-Bu
=
2O (1 equiv)
Boc
(0.1 equiv)
DMAP
CH2Cl2, r.t.
68–79% yield
X
Br
X
+
H
O
B(OH) 2
Y
Y
CO2t-Bu
C CN N
2R CO 1
R
C
2

Table of Contents VII
1333 V. D. B. Bonifácio*
J. Morgado
U. Scherf
1337 A. R. Katritzky*
N. E. Abo-Dya
S. R. Tala
E. H. Ghazvini-Zadeh
K. Bajaj
S. A. El-Feky
1341 M. Ueda
H. Miyabe
M. Torii
T. Kimura
O. Miyata*
T. Naito*
1345 R.-Y. Tang
P.-S. Luo
X.-G. Zhang
P. Zhong
J.-H. Li*
Synthesis of Thiosulfonate-Bridged Bromofluorene Endcapping Reagents
Efficient and Selective Syntheses of S-Acyl and N-Acyl Glutathiones
HO
O
O O
HN
R
NH
HO
O
N
H
O
SH
N-acyl-glutathiones
= α−amino alkyl, aryl
R
HO
O O HN
NH 2
1-(4-nitrobenzoyl)-
i.
1H-benzotriazole
HO
1-acyl-1H-benzotriazole
ii.
pyrrolidine
iii.
O
N
H
O
SH
1-acyl-1H-benzotriazole
HO
O O HN
NH 2
HO
O
N
H
O
S
R
O
S-acyl-glutathiones
= α−amino alkyl, aryl
R
Indium(I)-Mediated Radical Carbon–Carbon Bond-Forming Reaction in
Aqueous Media
InCl 3
CuCl disproportionation
H2O
RI
InIn
In(0)
InCl3 + R
2
MeO2C
R
EtO 2C
R
NX
PhO 2S
Silver-Catalyzed Tandem Ammonolysis–Cyclization of
2-Alkynylbenzenamines with Tetraalkylthiuram Disulfides to
4-Methylene-4H-benzo[d][1,3]thiazin-2-amines
R 2
R
NH2 1 +
R 3
S
S N
R3 S N
S
R 3
R 3
NX
R
AgBF4
DMSO, 80 °C
R 1
N
R 2
S
N R3
R 3
Letters

Letters
VIII Table of Contents
1351 T. Wang
X.-G. Huang
J. Liu
B. Li
J.-J. Wu
K.-X. Chen
W.-L. Zhu
X.-Y. Xu*
B.-B. Zeng*
1355 C. Tao*
W. Liu
A. Lv
M. Sun
Y. Tian
Q. Wang
J. Zhao*
1359 M. Kitamura*
K. Shiomi
D. Kitahara
Y. Yamamoto
T. Okauchi
1363 M. D’Auria*
R. Racioppi
O. A. Attanasi
F. Mantellini
An Efficient One-Pot Synthesis of Substituted 2-Aminothiophenes via
Three-Component Gewald Reaction Catalyzed by L-Proline
R 1
R 2
O
+
R 3
CN
+ S 8
R 3 = CO 2Et, CN
L-proline (10 mol%)
DMF, 60 °C
R 1
R 3
R
S
2 2 NH
examples
15
to 98% yield
up
Room-Temperature Copper-Catalyzed Synthesis of Primary Arylamines
from Aryl Halides and Aqueous Ammonia
R
X = I, Br
X
+
NH 3⋅H 2O
CuI, K 3PO4, DMF
room temperature
R
NH 2
examples
23
yield
11–98%
Pinacol Coupling of 2,2′-Biaryldiketone: An Application for the Synthesis of
Enantiopure 3,4-Dihydrodibenzo[c,g]phenanthrene-3,4-diol Derivatives
R
O
R
O
TiCl 4, Zn
CH2Cl2 THF,
°C –10
>99% ee >99% ee
Unusual [4+2]-Cycloaddition Reaction between Electron-Poor
1,2-Diaza-1,3-dienes and Electron-Poor Alkenes: Useful Entry to Novel
Tetrahydropyridazines
EWG 1 N N
R 1
EWG 2
+
R 4
R 5
EWG 3
R
R
OH
OH
N N
EWG 1
R1 EWG2 H
R4 H
R5 EWG3

Table of Contents IX
1367 E. Moreno-Clavijo
A. T. Carmona*
A. J. Moreno-Vargas
E. Álvarez
I. Robina*
1371 C. Beyer
H.-A. Wagenknecht*
1377 Y. He
C. R. Goldsmith*
1381 D. T. Patoilo
A. M. S. Silva*
J. A. S. Cavaleiro
Synthesis of Novel 3-Amino(Hydroxy)methyl-L-fuco-Azafagomines as Leads
for Selective Inhibitors of a-L-Fucosidases
D-lyxose
Me
HO HO
H
N
NH
R
functionalizable group
R = OH, NH2
lead for selective
new
inhibitors
α-L-fucosidase
Synthesis of DNA with Spirobenzopyran as an Internal Covalent
Modification
O
O
O
O
O
N
NH
N
O
N
N
N O NO2
The Halogenation of Aliphatic C–H Bonds with Peracetic Acid and Halide
Salts
O
O
OH
NaCl ,
r.t., H2O
Regioselective 3-Nitration of Flavones: A New Synthesis of 3-Nitro- and
3-Aminoflavones
O
O
R
NH 4NO 3
TFAA
O
O
NO2
Cl
R
HCO2NH4 A:
Pd/C
Sn (powder)
B:
(aq) HCl
O
O
NH2
R
Letters

Letters
X Table of Contents
1386 E. Fernández
W. Frey
J. Pietruszka*
1389 K. C. Majumdar*
A. Taher
R. K. Nandi
1394 P. Kula*
A. Spadło
M. Żurowska
R. Dąbrowski
1397 J. Velcicky*
D. Pflieger
Synthesis of Enantiomerically Pure Oxiranylboronic Esters
R
O
B
O
Ph
Ph
Ph Ph
OMe
OMe
R = n-C 5H 11, Ph, CH 2OH
epoxidation
method
R O
O
B
O
Ph
Ph
Ph Ph
OMe
OMe
O R
+
yield
35–95%
= 93:7 to 0:100
dr
O
B
O
Ph
Ph
Ph Ph
Copper(II) Acetate Promoted Intramolecular Carboamination of Alkenes:
An Efficient Synthesis of Pentacyclic Sultams
O
X
H
N
S
O O
R
Synthesis of New Chiral Smectic Mesogenes with 4-(2-Phenylethyl)biphenyl
and 4-[2-(3-Fluorophenyl)ethyl]biphenyl Molecular Cores
BnO Br
5 or 7 steps
R
O
X
R = C 3F 7CH 2OC nH 2nO- where n = 2–6 X = F or H
Synthesis of 3-Chloro-4-fluoro-7,8-dihydro-6H-isoquinolin-5-one and Its
Derivatives
Cl
N
F O
Cl
N
F
N
S
O
O
R
X
O
O
H
OMe
OMe
C6H13

Table of Contents XI
1402 S. Santoro
B. Battistelli
B. Gjoka
C.-w. S. Si
L. Testaferri
M. Tiecco
C. Santi*
1407 K. C. Majumdar*
B. Sinha
I. Ansary
S. Chakravorty
1412 H. Bian
J. Li
C. Li
G. Wang
Z. Duan
X. Jia*
1415 H. Zhang
M.-G. Chen
C.-X. Lian
W.-C. Yuan
X.-M. Zhang*
Oxidation of Alkynes in Aqueous Media Catalyzed by Diphenyl Diselenide
R 1 R 2 (NH4)2S2O8
(PhSe)2 cat
R 1
O
O
R 2 = H
R 2
gel silica
R3OH Molecular Iodine Mediated Intramolecular Cyclization: An Efficient
Method for the Synthesis of Benzoxepine Derivatives
R CHO
OH
R
I
MeO
O
O
O
H
O
R = t-Bu, Me, OMe, H H
R
Metallic Samarium Promoted Self-Coupling of Baylis–Hillman Adducts to
Functionalized 1,5-Hexadienes in the Presence of the I 2/ClCO 2Et/BiCl 3
System
Ar
OH
H
Sm/ClCO2Et/BiCl3/I2 COOMe
THF, reflux
or
I
I
COOMe Ar
H
COOMe
Remarkably Mild and Efficient Cetrimonium Bromide Catalyzed
Friedel–Crafts Amidoalkylation of Sesamols with N-Boc Imines
Generated In Situ in Aqueous Medium
O
O
R 1
OH
+
NHBoc
R 2 SO2Ar
Na2CO3
(10 mol%)
CTAB
H 2O, 30 °C
Ar
O
O
R 1
OH
R 2
R 1
up to 97%
O
NHBoc
OH
OR 3
Letters

Letters
Spotlights
XII Table of Contents
1418 Z. Chen
J. Zhu
H. Xie
S. Li
Y. Wu*
Y. Gong*
1421 S. Mięsowicz
W. Chaładaj
J. Jurczak*
1426 Compiled by
Garima
1428 Compiled by
Y. Wang
A Novel Method for the Synthesis of 2-Trifluoromethylindoles from
N-(o-Haloaryl)alkynylimines
F 3C
I
N
R 2
Pd(PPh3)2Cl2 (10 mol%)
equiv), H2O (1 equiv)
(2 4 3PO K
R
mL), 60 °C, 0.5 h
DME (2 1 R1 Oxo-Diels–Alder Reaction of Danishefsky’s Diene with Aldehydes, Catalyzed
by Chiral Tridentate Chromium(III)–Schiff Base Complexes
TMSO
OMe
catalyst (1 mol%)
1)
°C, 12 h 50
+ O
O TFA 2)
Triphenylphosphine Dibromide
R
O R
up to 99%
yield
up to 97%
ee
2-Cloro-1,3-Dimethylimidazolinium Chloride
O
N
H
O
N
R 2
Cr
CF 3
O
catalyst
BF4
2
H2O

Table of Contents XIII
1430 Erratum
XV Forthcoming Articles
Author Index
Abo-Dya, N. E. 1337
Álvarez, E. 1367
Ansary, I. 1407
Attanasi, O. A. 1363
Bajaj, K. 1337
Battistelli, B. 1402
Beyer, C. 1371
Bian, H. 1412
Bonifácio, V. D. B. 1333
Carmona, A. T. 1367
Catir, M. 1319
Cavaleiro, J. A. S. 1381
Chaładaj, W. 1421
Chakravorty, S. 1407
Chen, K.-X. 1351
Chen, M.-G. 1415
Chen, Z. 1418
Cox, D. J. 1315
Dąbrowski, R. 1394
D’Auria, M . 1363
Duan, Z. 1412
Dya, N. A. 1337
El-Feky, S. A. 1337
Fairbanks, A. J. 1315
Fernández, E. 1386
Franco, F. 1323
Frey, W. 1386
Fülöp, F. 1302
Garima 1426
Ghazvini-Zadeh, E. H. 1337
Gjoka, B. 1402
Goldsmith, C. R. 1377
Gong, Y. 1418
He, Y. 1377
Huang, X.-G. 1351
Hudhomme, P. 1331
Jia, X. 1412
Jurczak, J. 1421
Katritzky, A. R. 1337
Kilic, H. 1319
Kimura, T. 1341
Kiss, L. 1302
Kitahara, D. 1359
Kitamura, M. 1359
Kula, P. 1394
Li, B. 1351
Li, C. 1412
Li, J. 1412
Li, J.-H. 1345
Li, S. 1418
Lian, C.-X. 1415
Liu, J. 1351
Liu, W. 1355
Lo Re, D. 1323
Luo, P.-S. 1345
Lv, A. 1355
Majumdar, K. C. 1389, 1407
Mantellini, F. 1363
Mięsowicz, S. 1421
Miyabe, H. 1341
Miyata, O. 1341
Moreno-Clavijo, E. 1367
Moreno-Vargas, A. J. 1367
Morgado, J. 1333
Naito, T. 1341
Nandi, R. K. 1389
Okauchi, T. 1359
Parsons, T. B. 1315
Patoilo, D. T. 1381
Pflieger, D. 1397
Pietruszka, J. 1386
Racioppi, R. 1363
Rahimi, A. 1327
Robina, I. 1367
Santi, C. 1402
Santoro, S. 1402
Scherf, U. 1333
Schmidt, A. 1327
Shiomi, K. 1359
Si, C.-w. S. 1402
Silva, A. M. S. 1381
Sinha, B. 1407
Spadło, A. 1394
Sun, M. 1355
Taher, A. 1389
Tala, S. R. 1337
Tamayo, J. A. 1323
Tang, R.-Y. 1345
Tao, C. 1355
Testaferri, L. 1402
Tian, Y. 1355
Tiecco, M. 1402
Torii, M. 1341
Ueda, M. 1341
Velcicky, J. 1397
Wagenknecht, H.-A. 1371
Wang, G. 1412
Wang, Q. 1355
Wang, T. 1351
Wang, Y. 1428
Wu, J.-J. 1351
Wu, Y. 1418
Xie, H. 1418
Xu, X.-Y. 1351
Yamamoto, Y. 1359
You, S.-L. 1289
Yuan, W.-C. 1415
Zeng, B.-B. 1351
Zeng, M. 1289
Zhang, H. 1415
Zhang, X.-G. 1345
Zhang, X.-M. 1415
Zhao, J. 1355
Zhong, P. 1345
Zhu, J. 1418
Zhu, W.-L. 1351
Żurowska, M. 1394
Addenda and Errata