Post on 28-Jan-2021
Imprimatur:
Date, Signaturetc1618st.fm 9/21/18
Accounts andRapid Communications in Chemical Synthesis
2018Vol. 29, No. 16
Oktober ISyn lett
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Synlett 2018, 29, 2081–2086DOI: 10.1055/s-0037-1610161
J. K. VandavasiS. G. Newman*University of Ottawa, Canada
Syn lett
as
A High-Throughput Approach to Discovery: Heck-Type Reactivity with Aldehydes
R
O
HR'
X+R
O
R'
conditions
Ni(cod)2Triphos
TMP
Metal?
Ligand?
(Pseudo)halide?
Base?
OTf
carbonyl-Heck reaction
HTE
Synpacts
2081
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Synlett 2018, 29, 2087–2092DOI: 10.1055/s-0037-1610025
G. Chen*Y. YuX. Huang*Dongguan University of Technol-ogy, P. R. of ChinaFujian Institute of Research on the Structure of Matter, P. R. of China
Palladium-Catalyzed Annulation via Acyl C–H Bond Activation
H
O
X
R1
R2
R1
R2
O
Pd
Ph CO2R8
N2
X = Cl, Br, I
OO
Ph
OR8
R6
O
R5
R4R3
O
O
Ar Ar
ArAr
Ar
Ar
Ar
Acyl C-H Bond Cleavage
Synpacts
2087
Imprimaturhttps://doi.org/10.1055/s-0037-1610025https://doi.org/10.1055/s-0037-1610161
VI
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ted.
Synlett 2018, 29, 2093–2107DOI: 10.1055/s-0037-1610531
Y. Kuninobu*Kyushu University, Japan
Syn lett
Syn lett
s st
Development of Novel C–H Bond Transformations and Their Application to the Synthesis of Organic Functional Molecules
N
N
O
N
N
O
n
R
R
C–H Transformations
Regiocontrol Trifluoromethylation Organic functional materials
N
N
Ir NR2
O
N N
O
H H hydrogenbonds
N
MeO
HON
CF3
H
Account
2093
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Synlett 2018, 29, 2108–2116DOI: 10.1055/s-0037-1609627
M. BarbazangesL. Fensterbank*Sorbonne Université, France
as
The Invention of New Methodologies: An Opportunity for Dating Nat-ural Products
N
N
O
a-methyldeoxyvasicinone capnellene
H H
MeHCO2HHO2C (2S,3R)-(+)-roccellic acid
CO2HHO2C
(2R,3R)-(+)-sphaeric acid
HO
OH
epi-valeneomerin B
AcOO
sabina ketone
SO
O
passion fruit aroma
Au S SO O
p-Tolp-Tol
Account
2108
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Synlett 2018, 29, 2117–2119DOI: 10.1055/s-0037-1610998
Cover Page: Atropisomerism – In Memoriam Kurt Mislow
Cluster2117
https://doi.org/https://doi.org/10.1055/s-0037-1609627https://doi.org/10.1055/s-0037-1610531
VII
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Synlett 2018, 29, 2120–2121DOI: 10.1055/s-0037-1610998
J. S. Siegel*Tianjin University, P. R. of China
Syn lett
Syn lett
s st
Cluster Preface: Atropisomerism
Cluster2120
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Synlett 2018, 29, 2122–2125DOI: 10.1055/s-0037-1610908
J. S. Siegel*Tianjin University, P. R. of China
as
Prologue: Atropisomerism
HO2C
HO2C NO2
NO2 NO2
NO2HO2C
HO2C
Cluster
2122
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Synlett 2018, 29, 2126–2130DOI: 10.1055/s-0037-1610110
M. MatsuokaA. IidaO. Kitagawa*Shibaura Institute of Technolo-gy, Japan
α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho-Substituted Phenyl Groups: Relation between Diastereo-selectivity and the ortho-Substituent
N
N
C2H5
O X
N
N
O X
Me
R
X = F, Cl, Me, Br, Et, I, i-Pr, CF3
diastereoselectivitylow high
12 examples (85–98%)
axial chirality
central chirality
axial chirality
1) LiHMDS2) R-Y
THF, –20 °C
Cluster
2126
https://doi.org/10.1055/s-0037-1610110https://doi.org/10.1055/s-0037-1610908https://doi.org/10.1055/s-0037-1610998
VIII
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Synlett 2018, 29, 2131–2136DOI: 10.1055/s-0037-1610207
C. NiM. WangL. You*Fujian Institute of Research on the Structure of Matter, P. R. of China
Syn lett
Syn lett
s st
Dynamic Covalent Chemistry within Biphenyl Scaffolds: Effects from Endocyclic to Exocyclic Sulfonamides
Cluster
2131
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Synlett 2018, 29, 2137–2140DOI: 10.1055/s-0037-1609869
S. Toyota*T. SaibaraK. FujiseT. OkiT. IwanagaTokyo Institute of Technology, Japan
as
Synthesis and Conformational Analysis of 10-Mesitylanthracene-1,8-diyl Oligomers
Mes
Br Br Ni(cod)2bipy, cod
MesMes
Mes
n–2
oligomerization
StructureConformation
tolueneDMF
7.7–10.2% n = 2–4
Cluster
2137
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Synlett 2018, 29, 2141–2146DOI: 10.1055/s-0037-1609868
H. Tabata*Y. TsujiT. YonedaT. TasakaT. OshitariH. Takahashi*H. Natsugari*Teikyo University, JapanAffinity Science Corporation, JapanTokyo University of Science, Japan
Atropisomerism in the 2,3,4,5-Tetrahydro-1H-1,5-benzodiazepine Nucleus: Effects of Central Chirality at C3 on the N-Mesylation Reaction
CH3SO2Cl base
boat-like
CH3SO2ClN
N
3
A
B
N
N6
3
ps.eq.
ps.eq.
chair-like
boat-like
aS*
S*
aR*
S*
N
HN
HH
H
HH
36
from less hindered side
convex
concave
thermodynamic
kinetic
6
H3CSO2
H3CSO2
5
5
Cluster
2141
https://doi.org/10.1055/s-0037-1609868https://doi.org/10.1055/s-0037-1609869https://doi.org/10.1055/s-0037-1610207
IX
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Synlett 2018, 29, 2147–2154DOI: 10.1055/s-0037-1610190
Y. IshigakiT. IwaiY. HayashiA. NagakiR. KatoonoK. FujiwaraJ.-i. YoshidaT. Suzuki*Hokkaido University, Japan
Syn lett
Syn lett
s st
Transmission of Point Chirality to Axial Chirality for Strong Circular Dichroism in Triarylmethylium-o,o-dimers
Cluster
2147
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Synlett 2018, 29, 2155–2160DOI: 10.1055/s-0037-1609581
A. N. DinhR. R. NoorbeheshtS. T. ToenjesA. C. JacksonM. A. SaputraS. M. MaddoxJ. L. Gustafson*San Diego State University, USA
as
Toward a Catalytic Atroposelective Synthesis of Diaryl Ethers Through C(sp2)–H Alkylation with Nitroalkanes
O
O
O R1
R2 Cat. C2 (10 mol %)Cs2CO3 (10 equiv)NO2Me (10 equiv)0.1 M PhMe, 36 h
- Up to 80% yield- Up to 85:15 er
99:1 via trituration
H O
O
O R1
R2
Me
NH
N
O
NH
O NH
CF3
CF3
Br
Cat. C2
6 examples
Cluster
2155
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Synlett 2018, 29, 2161–2166DOI: 10.1055/s-0037-1609908
A. PaganoE. MarottaA. MazzantiG. Petrillo*C. TavaniM. Mancinelli*University of Bologna, ItalyUniversity of Genova, Italy
Stereodynamic Analysis of New Atropisomeric 4,7-Di(naphthalen-1-yl)-5,6-dinitro-1H-indoles
Cluster
2161
https://doi.org/10.1055/s-0037-1609908https://doi.org/10.1055/s-0037-1609581https://doi.org/10.1055/s-0037-1610190
X
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Synlett 2018, 29, 2167–2170DOI: 10.1055/s-0037-1610635
Y. Nagata*Y. ShimadaT. NishikawaR. TakedaM. UnoT. Ogoshi*M. Suginome*Kyoto University, JapanKanazawa University, Japan
Syn lett
Syn lett
s st
A Planar-Chiral Pillar[5]arene-Based Monophosphine Ligand with Induced Chirality at the Biaryl Axis
Cluster
2167
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Synlett 2018, 29, 2171–2175DOI: 10.1055/s-0037-1610551
B. MátravölgyiS. DeákZ. ErdélyiT. HergertP. Ábrányi-BaloghF. Faigl*Budapest University of Technol-ogy and Economics, Hungary
as
Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions
+ Et2ZnH
O
N
F3COH
N
F3C
NR1R2
OH
ArAr
ArAr
NR1R2
5%
5%
or the regioisomer H
EtOH
ee up to 96%
Cluster
2171
Thi
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Synlett 2018, 29, 2176–2180DOI: 10.1055/s-0037-1610233
C. FischerC. Sparr*University of Basel, Switzerland
Configurationally Stable Atropisomeric Acridinium Fluorophores
Cluster2176
https://doi.org/10.1055/s-0037-1610233https://doi.org/10.1055/s-0037-1610551https://doi.org/10.1055/s-0037-1610635
XI
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Synlett 2018, 29, 2181–2184DOI: 10.1055/s-0037-1610630
H. ZouC. HuK. ChenG. XiaoX. Peng*Nanjing University of Science and Technology, P. R. of China
Syn lett
Syn lett
s st
Cobalt Vanadium Oxide Supported on Reduced Graphene Oxide for the Oxidation of Styrene Derivatives to Aldehydes with Hydrogen Per-oxide as Oxidant
OO
CoV/rGO
R1R2 R1 O
catalyst (0.02 g), 65 °C, MeCN (5 mL)
H2O2 (30 wt%, 3 equiv), 6 h recyclable metal complexoxide catalyst
up to 96% yield
16 examples
R1 = aryl
R2 = H, NO2, Ph
Letter
2181
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Synlett 2018, 29, 2185–2190DOI: 10.1055/s-0037-1610272
J. NandiM. L. WitkoN. E. Leadbeater*University of Connecticut, USA
as
Combining Oxoammonium Cation Mediated Oxidation and Photo-re-dox Catalysis for the Conversion of Aldehydes into Nitriles
Letter
2185
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Synlett 2018, 29, 2191–2194DOI: 10.1055/s-0037-1610653
S. GaoY. MaW. ChenJ. Luo*Ningbo University, P. R. of China
Pd-Catalyzed Oxidation of Aldimines to Amides
Pd(OAc)2, TBHP
21 examplesup to 85% yield
N
R2
R1
NH
R2
R1
O
R1 = Br, Cl, F, Me, NO2R2 = CF3, NO2, COMe, Br, Cl, F, Me, t-Bu, OCF3, OMe
Letter
2191
https://doi.org/10.1055/s-0037-1610653https://doi.org/10.1055/s-0037-1610272https://doi.org/10.1055/s-0037-1610630
XII
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Synlett 2018, 29, 2195–2198DOI: 10.1055/s-0037-1610245
N. N. LeA. M. RodriguezJ. R. AlleynM. R. Gesinski*Southwestern University, USA
Syn lett
Syn lett
s st
Synthesis of 1,4-Diketones via Titanium-Mediated Reductive Homocoupling of -Haloketones
RX
O RX
O R
O
R
O
+
Ti(OiPr)4 + EtMgBr
"Ti(OiPr)3"
11 examples22–90%
R = aryl or heteroaromaticX = Cl or Br
Letter
2195
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Synlett 2018, 29, 2199–2202DOI: 10.1055/s-0037-1610234
Z.-G. XuY. DingJ.-P. MengD.-Y. TangY. LiJ. LeiC. Xu*Z.-Z. Chen*Chongqing University of Arts and Sciences, P. R. of ChinaUniversity of Electronic Science and Technology of China, P. R. of China
as
Facile Construction of Hydantoin Scaffolds via a Post-Ugi Cascade Re-action
R1 NH2
COOH
R3 N
O
N
R2
R1
O
R2 CHO R3 N
(2) K2CO3, CH3CN MW, 100 °C, 10 min
(1) MeOH, r.t. without purification
17 examples, yield 42–77%Two steps and one purificationShort reaction times
Atom economyMicrowave irradiation
One-pot protocol
leaving group
R1 = Ar
R2 = Ar
R3 = Ar, Alkyl
Letter
2199
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Synlett 2018, 29, 2203–2207DOI: 10.1055/s-0037-1609623
S. WangY. YuJ. Wen*X. Zhang*Southern University of Science and Technology, P. R. of China
Iridium/f-Amphox-Catalyzed Asymmetric Hydrogenation of Styrylglyoxylamides
[Ir(COD)Cl]2 (0.05 mol%)L1 (0.11 mol%)
O
N
HN
FePh2P
L1 f-amphox
OHN
O
R2R1
HN
O
OH
R2R1
DCE, KOHH2 (20 atm)
r.t., 12 h
NO
COOH
NH
O
Obenzazepril
TON up to 10000
16 examples96–99% yield94–98% ee
Letter
2203
https://doi.org/10.1055/s-0037-1609623https://doi.org/10.1055/s-0037-1610234https://doi.org/10.1055/s-0037-1610245
XIII
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Synlett 2018, 29, 2208–2212DOI: 10.1055/s-0037-1610247
S. NandyA. GhatakA. K. DasS. Bhar*Jadavpur University, India
Syn lett
Syn lett
s st
Chemoselective and Metal-Free Synthesis of Aryl Esters from the Cor-responding Benzylic Alcohols in Aqueous Medium Using TBHP/TBAI as an Efficient Catalytic System
tBuOOH (2 mol equiv)(Bu)4N+I– (20 mol%)
Imidazole (2 mol equiv)MeOH H2O, 8 h, 80 °C
COOMe
OOH
(86%)
OOH
(88%)
Me O R OH
OOH
tBuOOH (2 mol equiv)(Bu)4N+I– (20 mol%)
Imidazole (2 mol equiv)H2O, 8 h, 80 °C
R = MeR = H
Letter
2208
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https://doi.org/10.1055/s-0037-1610247