synlett 10/2010 - Thieme Chemistry

SYNLETT
1431 T. Schwabe
R. Huenerbein
S. Grimme*
1442 B. Xu*
G. B. Hammond*
1455 S. Bayindir
E. Erdogan
H. Kilic
N. Saracoglu*
Accounts and 2010
Rapid Communications in No. 10
Synthetic Organic Chemistry June II
Large Molecules – Small Energies: Challenges for Contemporary Quantum
Chemistry
From Vinylogation to Alkynylogation: Extending the Reactivity of Enolates
R 1
R5X R1 R2 O – M +
OR3 R4 R
CHO
2
COOR3 R5 M+ = (n-Bu) 4N +
M + = Li +
R 1
M + = (n-Bu) 4N +
R 2
COOR 3
EWG
EWG
R 1
M + = Li +
F +
R 2
COOR 3
An Efficient Synthesis of New Aza-Substituted Indoles via Michael-Type
Addition
N
O
Ph Ph
F
R 4
R 1
OH
R 2
COOR 3
Accounts
Letters

Letters
VI Table of Contents
1459 A. Ghoshal
A. R. Sarkar
G. Manickam
R. S. Kumaran
J. Jayashankaran*
1463 S. Paul
R. Jana
J. K. Ray*
1469 A. Alizadeh*
Z. Noaparast
H. Sabahnoo
N. Zohreh
1473 L. Jean-Gérard
F. Macé
H. Dentel
A. Ngoc Ngo
S. Collet*
A. Guingant*
M. Evain
Rhodium-Catalyzed Asymmetric Hydrosilylation of Ketones Employing a
New Ligand Embodying the Bis(oxazolinyl)pyridine Moiety
H HO
O
Rh catalyst, Ph 2SiH 2, AgBF 4
THF, 10 °C
94% yield, 98% ee
O
N
(S)
R
N
Rh
Cl Cl
Cl
Rh catalyst
Palladium-Catalyzed Intramolecular C–H Activation: A Synthetic Approach
towards Polycyclic Aromatic Hydrocarbons
Br
CHO
Br
OH
An Unprecedented and Concise Method for the Synthesis of
1,3-Thiazino-[3,4a][1,3]benzimidazoles via a Three-Component Reaction
R
NH 2
NH2
+
Ar NCS
+
H
CO2Me
CH2Cl 2–toluene
reflux, 10 h
A New Synthesis of (R)-(–)-Sumanirole (PNU-95666E)
Ph
N
O N
O
O
epoxidation
MCPBA
Ph
N
O
O N
O
O
steps
R
HN
Ar
N
N
N
N
O
N
sumanirole
S
O
(S)
NHMe
•HCl

Table of Contents VII
1477 A. A. Esmaeili*
R. Hosseinabadi
A. Habibi
1481 C. Chaulet
C. Croix
J. Basset
M.-D. Pujol
M.-C. Viaud-Massuard*
1485 S. Sobhani*
S. Rezazadeh
1489 M. Ayaz
B. Westermann*
An Efficient Synthesis of Highly Functionalized 4H-Pyrano[3,2-d]isoxazoles
via Isocyanide-Based Three-Component Reaction
R 1 N C: +
CO 2R 2
CO2R 2
+
Ph
N O
O
MeCN
reflux
Ph
N
O
CO2R 2
O
CO 2R 2
Desulfonylation of Indoles and 7-Azaindoles Using Sodium tert-Butoxide
X
N
R
SO2Ph
NaOt-Bu
dioxane
tube
sealed
80 °C
X
N H
X = CH, N
HClO 4–SiO 2 as a Novel and Recyclable Catalyst for the Phospha-Michael
Addition of Phosphorous Nucleophiles to a,b-Unsaturated Malonates
R 2
X
R1 P(OEt)3
+
Y
R1 aryl, heteroaryl, alkyl
=
R2 alkyl, H =
= CN, CO2Et, NO2
X
= CN, CO2Et, H
Y
HClO 4–SiO 2 (3 mol%)
solvent-free
R
O
P(OEt)2
Enantioenriched Naphthoquinone Mannich Bases by Organocatalyzed
Nucleophilic Additions to in situ Formed Imines
O
O
OH
10 mol% cat.
α-amidosulfones
N
H
Me2N
S
N
H
R 1
R 2
Y
X
NH
R 1
O
O
OAc
R
up to 94%
yields
up to 65%
ee
NHPG
Letters

Letters
VIII Table of Contents
1493 F. Voss
T. Bach*
1497 P. Wessig*
K. Möllnitz
S. Hübner
1501 N. Purkayastha
G. Haufe*
1505 M. Koley
M. Schnürch
M. D. Mihovilovic*
An Ethynyl-Substituted 1,5,7-Trimethyl-3-azabicyclo[3.3.1]nonan-2-one as a
Versatile Precursor for Chiral Templates and Chiral Photocatalysts
O
H
N
Ar
ArX [Pd 0 ]
Et 3N [CuI]
O
H
N
steric shield and/or photocatalytic unit
ArN 3
Et3N [CuI]
A Short and Efficient Route from myo- to neo-Inositol
HO
HO
OH
OH
OH
OH
9 steps
51%
HO
HO
OH
OH
OH
OH
O
H
N
N
N
Ar
N
An Efficient Access to Conformationally Rigid Amino Acid Analogues with
a Piperidine Skeleton
NH2
N t-Bu CONHMe
H
O
N t-Bu CONHMe
H
t-Bu
i-BuO
N
NH2
O
O
NHMe
Selective and Facile Palladium-Catalyzed Amination of
2-Fluoro-4-iodopyridine in the 4-Position under Microwave Conditions
I
N
F
selective
cross-coupling
+
X
nucleophilic
no
substitution
HN
R2 R 1
2, (2 mol%),
Pd(OAc)
(2 mol%)
BINAP
3, toluene,
K2CO
°C, MW
180
R 2
N
N
R 1
F
(13 examples)
48–84%
R1 aryl, alkyl
=
R 2 = H, alkyl

Table of Contents IX
1511 S. Kim*
J.-I. Hwang
1515 A. Yanagisawa*
T. Koide
K. Yoshida
1519 Y.-S. Lu
Q. Li
Y. Wang
X.-S. Ye*
1525 O. Fatunsin
M. Shkoor
A. Riahi
P. Langer*
Anionic Cyclization of N-(trans-2,3-Diphenylaziridin-1-yl)imines:
Its Application to Sesquiterpene Synthesis via Consecutive Carbon–Carbon
Bond-Formation Approach
Azi
TBSO
N
N N
Li
Ph
Ph
Azi = trans-2,3-diphenylaziridinyl
–
H
OTBS
Selective Propargylation of Azo Compounds with Barium Reagents
R 1 N
N R1
+
R 2
X
R 3
Ba*
THF
R 1
NH
R 1 N
R
52–92%
3
Direct a-Selective Glycosylations of Acetyl-Protected 2-Deoxy- and
2,6-Dideoxythioglycosides by Preactivation Protocol
AcO
AcO
R
O
R = OAc or H
STol
BSM, Tf 2O
CH2Cl2, –72 °C
HO
Regioselective Synthesis of Highly Functionalized Arylphosphonates by
Cyclocondensation of 1,3-Bis(trimethylsilyloxy)buta-1,3-dienes with
3-Ethoxy-2-phosphonylalk-2-en-1-ones
Me3SiO
R2 OEt
O
P
+
O
OSiMe3
R 3
OEt
OEt
OR 1
TiCl 4
R 2
O
OH
P
O
O
R 3
OEt
OEt
OR 1
AcO
AcO
R
R 2
O
O
O
H
OTBS
Letters

Letters
X Table of Contents
1528 P. Ehlers
S. Reimann
S. Erfle
A. Villinger
P. Langer*
1533 O. Fatunsin
V. O. Iaroshenko*
S. Dudkin
M. Shkoor
D. Volochnyuk
A. Gevorgyan
P. Langer*
1536 C. R. Reddy*
B. Srikanth
1539 J. Laudien
E. Fouquet
C. Zakri
F.-X. Felpin*
Synthesis of 2-Aryl-3,4,5,6-tetrachloropyridines and 2,6-Diaryl-3,4,5trichloropyridines
by Site-Selective Suzuki–Miyaura Reactions of
Pentachloropyridine
Cl
Cl
Cl
Cl Cl N
Ar 1 B(OH)2
Ar 2 B(OH) 2
[Pd]
Cl
Cl
Cl
Ar N 2 Ar1 Synthesis of Chromeno[3,4-b]pyrrol-4(3H)-ones by Cyclocondensation of
1,3-Bis(trimethylsilyloxy)buta-1,3-dienes with 4-Chloro-3-nitrocoumarin
TMSO OTMS
R 2
Cl
O
OR 1
NO 2
O
1) TiCl4
R 2
2) H 2, Pd/C NH
O O
Synthesis of the Tetrahydropyran Subunit (C8–C20 Fragment) of
(–)-Dactylolide and (–)-Zampanolide
TBDPSO
OH
O
OMe
N
Me
steps
OBn
steps
HO
OH
O
O
O
OR 1
O
O R
20
O
O
= CHO, (–)-dactylolide
R
= CH(OH)NHCOC5H7, R
(–)-zampanolide
A Multi-Task Palladium Catalyst Involved in Heck–Reduction–Cyclization
Sequences for the Preparation of 4-Benzyl-1,2-dihydroisoquinolin-3-ones:
An Unusual Homogeneous–Heterogeneous Sustainable Approach
R 1
CN
CO 2Me + F4BN 2
R 2
HRC
Pd
R 2
R 1
NH
O
8

Table of Contents XI
1544 D. Fritz
S. Bräse*
1549 M. Rueping*
B. J. Nachtsheim
E. Sugiono
1554 G. L. Huang*
Y. P. Dai
1557 M. Kirihara*
A. Itou
T. Noguchi
J. Yamamoto
Solid-Phase Synthesis of (w-Aminoalkyl)peptoids Using Azide Chemistry
1) bromoacetic acid
2) H2N–R–N3 HN
NH2
repeat n–1 times
O
N 3
N
R
1) reduction
2) cleavage H2N
H
O
NH 2
H
n
n
R
N
(ω-aminoalkyl)peptoid
Direct Catalytic Benzylation of Hydroxycoumarin – Efficient Synthesis of
Warfarin Derivatives and Analogues
OH
R
O O
Ar
OH
O O
Ar
Ph
R
OH
OH
O O
OH
O O
phenprocoumone coumatetralyl
62%
mol% 0.5
catalyst
Solid-Phase Synthesis of Allosamidin
HO
HO
HO
AcO
OH
O
NHAc
HO
HO
OBn
O
NHCbz
OBn
O
NMe2
N
O
O
OBn
O
N
OH
O O O
HO
NHAc
HO
NMe2
OH
O
NMe2
N
mol% 5
catalyst
76%
OH
O O
Tantalum Carbide or Niobium Carbide Catalyzed Oxidation of Sulfides with
Hydrogen Peroxide: Highly Efficient and Chemoselective Syntheses of
Sulfoxides and Sulfones
R 1 S R 2
(0.02 equiv)
TaC
H2O2 (5 equiv)
30%
MeOH, 45 °C
(0.04 equiv)
NbC
H2O2 (4.5 equiv)
30%
EtOH, 60 °C
O
R 1 S R 2
O O
R 1 S R 2
Letters

Letters
Spotlights
XII Table of Contents
1562 S. Ushijima
H. Togo*
1567 P. Tundo*
C. R. McElroy
F. Aricò
1572 Compiled by
N. Yeole
1574 Compiled by
M. Mokhlesi
One-Pot Conversion of Aromatic Bromides and Aromatics into Aromatic
Nitriles
THF
DMF
I2, NH3
n-BuLi,
ArLi ArCN
ArCH(OLi)NMe2
ArX
X = Br, H
–70 °C or 0 °C
1 h, 0 °C
2 h, r.t.
Synthesis of Carbamates from Amines and Dialkyl Carbonates: Influence of
Leaving and Entering Groups
RNH2
RNHCOOMe
catalyst, base base
dimethyl carbonate
Thiocarbonylthio Compounds
t-BuOH
Silica-Functionalized Sulfonic Acid
RNHBoc

Table of Contents XIII
1576 Erratum
XVII Forthcoming Articles
Author Index
Alizadeh, A. 1469
Aricò, F. 1567
Ayaz, M. 1489
Bach, T. 1493
Basset, J. 1481
Bayindir, S. 1455
Bräse, S. 1544
Chaulet, C. 1481
Collet, S. 1473
Croix, C. 1481
Dai, Y. P. 1554
Dentel, H. 1473
Dudkin, S. 1533
Ehlers, P. 1528
Erdogan, E. 1455
Erfle, S. 1528
Esmaeili, A. A. 1477
Evain, M. 1473
Fatunsin, O. 1525, 1533
Felpin, F.-X. 1539
Fouquet, E. 1539
Fritz, D. 1544
Gevorgyan, A. 1533
Ghoshal, A. 1459
Grimme, S. 1431
Guingant, A. 1473
Habibi, A. 1477
Hammond, G. B. 1442
Haufe, G. 1501
Hosseinabadi, R. 1477
Huang, G. L. 1554
Hübner, S. 1497
Huenerbein, R. 1431
Hwang, J.-I. 1511
Iaroshenko, V. O. 1533
Itou, A. 1557
Jana, R. 1463
Jayashankaran, J. 1459
Jean-Gérard, L. 1473
Kilic, H. 1455
Kim, S. 1511
Kirihara, M. 1557
Koide, T. 1515
Koley, M. 1505
Kumaran, R. S. 1459
Langer, P. 1525, 1528, 1533
Laudien, J. 1539
Li, Q. 1519
Lu, Y.-S. 1519
Macé, F. 1473
Manickam, G. 1459
McElroy, C. R. 1567
Mihovilovic, M. D. 1505
Mokhlesi, M. 1574
Möllnitz, K. 1497
Nachtsheim, B. J. 1549
Ngoc Ngo, A. 1473
Noaparast, Z. 1469
Noguchi, T. 1557
Paul, S. 1463
Pujol, M.-D. 1481
Purkayastha, N. 1501
Ray, J. K. 1463
Reddy, C. R. 1536
Reimann, S. 1528
Rezazadeh, S. 1485
Riahi, A. 1525
Rueping, M. 1549
Sabahnoo, H. 1469
Saracoglu, N. 1455
Sarkar, A. R. 1459
Schnürch, M. 1505
Schwabe, T. 1431
Shkoor, M. 1525, 1533
Sobhani, S. 1485
Srikanth, B. 1536
Sugiono, E. 1549
Togo, H. 1562
Tundo, P. 1567
Ushijima, S. 1562
Viaud-Massuard, M.-C. 1481
Villinger, A. 1528
Volochnyuk, D. 1533
Voss, F. 1493
Wang, Y. 1519
Wessig, P. 1497
Westermann, B. 1489
Xu, B. 1442
Yamamoto, J. 1557
Yanagisawa, A. 1515
Ye, X.-S. 1519
Yeole, N. 1572
Yoshida, K. 1515
Zakri, C. 1539
Zohreh, N., 1469
Addenda and Errata