synlett 04/2005 - Thieme Chemistry

SYNLETT
545
The Pauson–Khand-Type Reaction Catalyzed by
Transition Metal Nanoparticles
K. H. Park, Y. K. Chung*
560
Cp*Ir Complex-Catalyzed Hydrogen Transfer
Reactions Directed toward Environmentally Benign
Organic Synthesis
K.-i. Fujita, R. Yamaguchi*
572
A Comment on the Gurjar Mechanism for Alkene
Isomerization Using the Grubbs Olefin Metathesis
Catalysts
C. D. Edlin, J. Faulkner, D. Fengas, C. K. Knight, J. Parker,
I. Preece, P. Quayle,* S. N. Richards
577
Synthesis of Polycyclic Lactams and Sultams by a
Cascade Ring-Closure Metathesis/Isomerization and
Subsequent Radical Cyclization
C. Bressy, C. Menant, O. Piva*
583
Reductive Alkylation of Aromatic Amines with Enol
Ethers
T. J. Reddy,* M. Leclair, M. Proulx
Accounts and 2005
Rapid Communications in No. 4
Synthetic Organic Chemistry March I
R1 R2 OH O
R1 R2 +
Cp*Ir catalyst
O
+
OH
Oppenauer-type oxidation
Cp*Ir catalyst
R1NH2 R2OH R1R2 +
N-Alkylation
NH + H2O HO
RNH2 +
HO
Cp*Ir catalyst
N-Heterocyclization
R N + 2 H2O
R
N
Cp*Ir catalyst
Transfer hydrogenation
R
N
H
R
R
OH
H
Y ( )
N
n
Br
Y = CO2, SO2
n = 1, 2
R
Br
OH H
Ru
Ph
Y ( ) Y
N
N
n ( ) n
Br
Cl
R
Ir
Cl
Cl
Cl
Ir
Cp*Ir catalyst
O
Y
N
OMe
NH2 (1.5 equiv)
NH
HOAc (1.0 equiv), NaBH(OAc)3 (1.5 equiv)
1,2-Dichloroethane, r.t., 50–98% yields
R = CN, Cl, F, NO2, CO2Et, COMe etc.
R
H
( ) n
Accounts
Letters

Letters
VI Table of Contents
587
Regio- and Enantioselective Synthesis of Novel
Functionalized Pyranopyrrolidines by 1,3-Dipolar
Cycloaddition of Carbohydrates
G. Bashiardes,* C. Cano, B. Mauzé
591
Sulfanyl Radical-Induced Cyclization of Linalyl
Acetate to the Iridane Skeleton: A Short Synthesis of
(±)-Dehydroiridomyrmecin
A. F. Barrero,* S. Arseniyadis, M. M. Herrador, J. F. Quílez del
Moral, J. F. Arteaga, E. M. Sánchez
595
Reactivity of PNA Thioesters in Chemical Ligation
Reactions
M. C. de Koning, M. van der Knaap, L. Petersen, H. van den Elst,
G. A. van der Marel, M. Overhand, D. V. Filippov*
599
Cu(I)-Catalyzed Cyclized Coupling Reaction of
o-Ethynylphenylphosphonic Acid Monoesters with
Allyl Bromide
P. Wei, Y.-X. Ding*
603
Asymmetric Michael Addition of Arylthiols to
a,b-Unsaturated Carbonyl Compounds Catalyzed by
Bifunctional Organocatalysts
B.-J. Li, L. Jiang, M. Liu, Y.-C. Chen,* L.-S. Ding, Y. Wu
607
TEMPO-Derived Task-Specific Ionic Liquids for
Oxidation of Alcohols
X.-E. Wu, L. Ma, M.-X. Ding, L.-X. Gao*
N
H
OAc
CO2Me
R′S
H
OAc
SR′
CO2Me
B
O
O
HS
N
N
H
B = G or T
SPh
+ H2N
O 0,1
O
RYNK
B
Comparison of ligation rates
gives insight in thioester reactivity
O
O
N
N
N
H
H
B = G or T
H
N
O 0,1
O
SH
RYNK
R 2
OH
P
OEt
O
Br
10 mol% CuI
DMF P O
O
R
OEt
2
R
+
1
2
1 R1 R 2
R 1
S
N N
R 5
R 2
R 1
S
N N
N
H
H
O
H
O
N
H
H
O
H
ArS R
N
H
Ph
ArS
n
4
R3 up to 99% yield; up to 85% ee on β-carbon, 60% ee on α-carbon
OH
R 1 R 2
O
N
O
O
N N
PF 6 –
NaOCl (1.24 equiv), KBr (10 mol%), PH = 8.6, 4 (1 mol%)
H
R 5
[bmim]PF6/H2O, 0 °C R 1 R 2
O
O
O

Table of Contents VII
611
A Homo-Proline Tetrazole as an Improved Organocatalyst
for the Asymmetric Michael Addition of
Carbonyl Compounds to Nitro-Olefins
C. E. T. Mitchell, A. J. A. Cobb, S. V. Ley*
615
Development of Chiral Catalysts by Asymmetric
Activation for Highly Enantioselective Diethylzinc
Addition to Imines
O
O
O
H.-L. Zhang, H. Liu, X. Cui, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong*
HN
Ar
1
H Et2Zn
SO2Tol Ar
N H
H
2
10 mol% L3ZnA1
HN
Et2Zn, ClCH2CH2Cl
–25 °C, 36 h Ar
3
H
619
Easy Copper-, Ligand- and Amine-Free Sonogashira
Coupling Reaction Catalyzed by Palladium on Carbon
at Low Catalyst Loading and by Exposure to Air
G. Zhang*
623
Regioselective Syntheses of Functionalized 2-Aminopyridines
and 2-Pyridinones through Nucleophile-
Induced Ring Transformation Reactions
A. Goel,* F. V. Singh, A. Sharon, P. R. Maulik
627
Enantioselective Synthesis of Cyanohydrins by a
Novel Aluminum Catalyst
B. M. Trost,* S. Martínez-Sánchez
631
An Efficient Synthesis of Cyclic b-Amino Acid
Derivatives as b-Turn Mimetics
T. Yamanaka,* M. Ohkubo,* M. Kato, Y. Kawamura, A. Nishi,
T. Hosokawa
up to 91% yield
up to 94% ee
R
O
O
R
Zn
N
N
L3ZnA1, R = 3,5-(CF3)2C6H3
R I + CH C
1% Pd/C (0.2 mol% Pd)
R
Na3PO4·12H2O (2 equiv)
R
1 C C R1 n
BocN
i-PrOH/H 2O, 80 °C
O
O
O Grubbs'
NaN(TMS) 2
catalyst LiOOH
N
O
allyl iodide n
(R)
BocN * N
n
(R)
O
BocN *
CH2Ph
(R)
(R)
CO2H
O
n = 1,2
CH2Ph
87–93%
n = 1,2
>98% ee
57–64%
>99% de
Ph
Ph
Letters

Letters
VIII Table of Contents
635
First Synthesis of (+)-Pteroenone: A Defensive
Metabolite of the Abducted Antarctic Pteropod
Clione antarctica
Y. Nakamura, H. Kiyota,* B. J. Baker, S. Kuwahara
637
Stereoselective Synthesis of Condensed Aza-D-homoestrone
Derivatives by 1,3-Dipolar Cycloaddition
E. Mernyák, G. Benedek, G. Schneider, J. Wölfling*
640
Pseudo-Geminally-Substituted [2.2]Paracyclophanes
as Spacers for Bisallenyl Sulfoxides and Sulfones
M. L. Birsa, P. G. Jones, S. Braverman, H. Hopf*
643
Dyotropic Rearrangements of Tetraazafulvalenes –
A New Approach to Aminosubstituted 1,4,5,8-
Tetraazanaphthalenes
F. Stöckner, C. Käpplinger, R. Beckert,* H. Görls
646
Highly Diastereoselective Desymmetrisation of Cyclic
meso-Anhydrides and Derivatisation to Mono-
Protected 1,4-Diols
A. C. Evans, D. A. Longbottom, M. Matsuoka, S. V. Ley*
649
Iodine-Catalysed Bohlmann–Rahtz Cyclodehydration
Reactions
M. C. Bagley,* C. Glover, D. Chevis
O
O N
Ar
HN
HN
Ar
R1 H
R2 H
RO 2C
Me
Bn
O
O
O OH
6 steps O OH
N
OH
OH
N
N N
O
O
NH 2
R
R
74%
1. PCMM, NEt3 –78 °C, 80–84%
2. DMDO, 40–42%
Ar
NH
NH
Ar
K10
DMF, 130 °C
24 h
1, CH2Cl2, –78 °C, 30 min
then TMSCHN2, 16 h
where 1 =
R'
HN
O
"(+)-Aux"
O
Bohlmann–Rahtz
cyclodehydration
I 2 (0.5–100 mol%)
EtOH, 0 °C or r.t.
(92 to >98%)
HN
HN
(+)-pteroenone
Ar
Ar
1 H
R
O
R2 H
O
RO 2C
Me
N
N
OMe
(+)-Aux
N
N
SO2CCl3
R
R
N R'
no SiO2 purification
SO2CCl3
Ar
NH
NH
Ar

Table of Contents IX
652
First Total Synthesis of the Irciniasulfonic Acids
A. P. Dobbs,* A. Venturelli, L. A. Butler, R. J. Parker
655
Synthesis of the C13-C23 Segment of Tedanolide
G. Ehrlich, M. Kalesse*
658
Nickel-Catalyzed Cross-Coupling of Diphenylphosphine
with Vinyl Bromides and Chlorides as a Route
to Diphenylvinylphosphines
M. O. Shulyupin, E. A. Chirkov, M. A. Kazankova,*
I. P. Beletskaya
661
(PhO) 3P·Cl2-Promoted Bischler–Napieralski-Type
Cyclization: a Mild Access to b-Carbolines
A. Spaggiari, P. Davoli, L. C. Blaszczak, F. Prati*
664
Enantiocontrolled Synthesis of a Chiral Building
Block via Diastereoselective Ring-Closing Metathesis
Y. Murakami, M. Shindo, K. Shishido*
667
Rhodium-Catalyzed Addition–Cyclization Reactions
of 5-Yn-1-ones with Arylboronic Acids
T. Miura, M. Shimada, M. Murakami*
R =
23
Irciniasulfonic acid
O
Ph 2PH
O
O
O
OH
R
+
Cl
N
H
– O3S OH
O
1
O OMe O
17'
17
or
O
13
OH
(+)-Tedanolide
Cl
Br
NH
R
O
O
O
O
OH
23
1–2 mol% Ni(acac) 2, Et 3N
DMF, 120 °C
(PhO) 3P·Cl 2
CH 2Cl 2, –30 °C
Ph2P
RO
TBSO
R
N
H
OR
17 13 OH
PPh 2
R' R'
R 1 O RCM
X
O
R 2
R 1
(50–98% yield)
OR2 64–82% de
HO2C
+ ArB(OH)2
MeO
R 1 O
O
Rh(I)Ln
X
R 1
OH
R 2
OR 2
Ar
OPMB
PPh2
N
R
Letters

Letters
Cluster
X Table of Contents
670
Dramatic Effect of Boron-Based Lewis Acids in Cross-
Metathesis Reactions
E. Vedrenne, H. Dupont, S. Oualef, L. Elkaïm,* L. Grimaud*
675
New Synthetic Models of Cytochrome P450: How
Different Are They from the Natural Species?
S. Kozuch, T. Leifels, D. Meyer, L. Sbaragli, S. Shaik,*
W.-D. Woggon*
685
Horner–Wadsworth–Emmons Reactions as a Facile
Entry to Biogenetic Key Substructures
J. Mulzer,* A. Sieg, C. Brücher, D. Müller, H. J. Martin
693
An Improved Synthesis of Optically Pure 4-Boc-5,6-
Diphenylmorpholin-2-one and 4-Cbz-5,6-Diphenylmorpholin-2-one
K. A. Dastlik, U. Sundermeier, D. M. Johns, Y. Chen,
R. M. Williams*
697
Investigation of the Biomimetic Synthesis of Emindole
SB Using a Fluorinated Polyene Cyclisation Precursor
J. S. Clark,* J. Myatt, L. Roberts, N. Walshe
700
Concise Synthesis of (±)-Smenochromene D
(= Likonide B)
B. S. Olson, D. Trauner*
t-BOCHN
+
OH
R1 R2 OH
TBS
* *
* *
*
X Me Y
N
Ru cat. (5 mol%)
OMe Lewis acid (10 mol%)
O toluene, 80 °C
12 h
F
Lewis acid
O
Me Me
Me
TBS
N Me
?
F
F
N Me
TBS
Me
Me
H
H
t-BOCHN
OMe
L. A.
O
Yield (%)
none 28
Ti(Oi-Pr) 4 0
Cy2BCl 84
Me
Me
OH
OH

Table of Contents XI
703
Biomimetic Tandem Cyclization Catalyzed by
Hg(OTf) 2 Affording Polycarbocycles
H. Imagawa, T. Iyenaga, M. Nishizawa*
706
Water-Soluble Diketopiperazine Receptors – Selective
Recognition of Arginine-Rich Peptides
P. Krattiger, H. Wennemers*
709
Tri-tert-butylphosphine [(t-Bu) 3]: An Electron-Rich
Ligand for Palladium in Cross-Coupling Reactions
Compiled by S. Reddy Dubbaka
711
Indium Tribromide: A Water-Tolerant
Green Lewis Acid
Compiled by Z.-H. Zhang
HO2C
HO2C
O
O
N
H
H
N
OMe Hg(OTf)2
(1 mol%)
OMe
CO2H H
N
CH3NO2
0 °C, 1 h
OMe
Hg(OTf)2
(1 mol%)
CH3NO2 r.t., 24 h
O
H
N
H
H
O
dye
H
O
N
H
CO2H
O
N H
O O
O
N
H
CO2H CO2H H
N
O
H
O
N
H
N
dye
O
Forthcoming Articles XVII
98%
OMe
OMe
58%
OMe
Cluster
Spotlights

XII Table of Contents
Author Index
Arseniyadis, S. 591
Arteaga, J. F. 591
Bagley, M. C. 649
Baker, B. J. 635
Barrero, A. F. 591
Bashiardes, G. 587
Beckert, R. 643
Beletskaya, I. P. 658
Benedek, G. 637
Birsa, M. L. 640
Blaszczak, L. C. 661
Braverman, S. 640
Bressy, C. 577
Brücher, C. 685
Butler, L. A. 652
Cano, C. 587
Chen, Y. 693
Chen, Y.-C. 603
Chevis, D. 649
Chirkov, E. A. 658
Chung, Y. K. 545
Clark, J. S. 697
Cobb, A. J. A. 611
Cui, X. 615
Dastlik, K. A. 693
Davoli, P. 661
de Koning, M. C. 595
Ding, L.-S. 603
Ding, M.-X. 607
Ding, Y.-X. 599
Dobbs, A. P. 652
Dupont, H. 670
Edlin, C. D. 572
Ehrlich, G. 655
Elkaïm, L. 670
Evans, A. C. 646
Faulkner, J. 572
Fengas, D. 572
Filippov, D. V. 595
Fujita, K.-i. 560
Gao, L.-X. 607
Glover, C. 649
Goel, A. 623
Gong, L.-Z. 615
Görls, H. 643
Grimaud, L. 670
Herrador, M. M. 591
Hopf, H. 640
Hosokawa, T. 631
Imagawa, H. 703
Iyenaga, T. 703
Jiang, L. 603
Jiang, Y.-Z. 615
Johns, D. M. 693
Jones, P. G. 640
Kalesse, M. 655
Käpplinger, C. 643
Kato, M. 631
Kawamura, Y. 631
Kazankova, M. A. 658
Kiyota, H. 635
Knight, C. K. 572
Kozuch, S. 675
Krattiger, P. 706
Kuwahara, S. 635
Leclair, M. 583
Leifels, T. 675
Ley, S. V. 611, 646
Li, B.-J. 603
Liu, H. 615
Liu, M. 603
Longbottom, D. A. 646
Ma, L. 607
Martin, H. J. 685
Martínez-Sánchez, S. 627
Matsuoka, M. 646
Maulik, P. R. 623
Mauzé, B. 587
Menant, C. 577
Mernyák, E. 637
Meyer, D. 675
Mi, A.-Q. 615
Mitchell, C. E. T. 611
Miura, T. 667
Müller, D. 685
Mulzer, J. 685
Murakami, M. 667
Murakami, Y. 664
Myatt, J. 697
Nakamura, Y. 635
Nishi, A. 631
Nishizawa, M. 703
Ohkubo, M. 631
Olson, B. S. 700
Oualef, S. 670
Overhand, M. 595
Park, K. H. 545
Parker, J. 572
Parker, R. J. 652
Petersen, L. 595
Piva, O. 577
Prati, F. 661
Preece, I. 572
Proulx, M. 583
Quayle, P. 572
Quílez del Moral, J. F. 591
Reddy Dubbaka, S. 709
Reddy, T. J. 583
Richards, S. N. 572
Roberts, L. 697
Sánchez, E. M. 591
Sbaragli, L. 675
Schneider, G. 637
Shaik, S. 675
Sharon, A. 623
Shimada, M. 667
Shindo, M. 664
Shishido, K. 664
Shulyupin, M. O. 658
Sieg, A. 685
Singh, F. V. 623
Spaggiari, A. 661
Stöckner, F. 643
Sundermeier, U. 693
Trauner, D. 700
Trost, B. M. 627
van den Elst, H. 595
van der Knaap, M. 595
van der Marel, G. A. 595
Vedrenne, E. 670
Venturelli, A. 652
Walshe, N. 697
Wei, P. 599
Wennemers, H. 706
Williams, R. M. 693
Woggon, W.-D. 675
Wölfling, J. 637
Wu, X.-E. 607
Wu, Y. 603
Yamaguchi, R. 560
Yamanaka, T. 631
Zhang, G. 619
Zhang, H.-L. 615
Zhang, Z.-H. 711