imprimatur: date, signature tc2318ss.fm 11/15/18 · efficient and versatile catalytic systems for...
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Imprimatur:
Date, Signaturetc2318ss.fm 11/15/18
Reviews and Full Papers in Chemical Synthesis
2018Vol. 50, No. 23
December ISyn thesis
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Synthesis 2018, 50, 4501–4524DOI: 10.1055/s-0037-1610284
U. GrošeljF. PožganB. ŠtefaneJ. Svete*University of Ljubljana, Slovenia
Syn thesis
as
Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)
R2
NN
R3 R1
R4
NN
R1
R2
R4
NN
R1
R4 R3
NN OR
4
R5
NN R1
R4
R3
Cu0, Cu+, or Cu2+
Review
4501
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Synthesis 2018, 50, 4525–4538DOI: 10.1055/s-0037-1610288
E. R. El-SawyA. B. AbdelwahabG. Kirsch*Université de Lorraine, France
Utilization of 1H-Indole-3-carboxaldehyde as a Precursor for the Synthesis of Bioactive Indole Alkaloids
Review
4525
Imprimaturhttps://doi.org/10.1055/s-0037-1610288https://doi.org/10.1055/s-0037-1610284
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VI
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Synthesis 2018, 50, 4539–4554DOI: 10.1055/s-0037-1611014
E. Martinez de MarigortaJ. M. de los SantosA. M. Ochoa de RetanaJ. Vicario*F. Palacios* University of the Basque Coun-try, Spain
Syn thesis
Syn thesis
s st
Multicomponent Reactions in the Synthesis of γ-Lactams
N
O
N
O
A+B+C...N
O
S
hort Review4539
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Synthesis 2018, 50, 4555–4568DOI: 10.1055/s-0037-1609943
A. CholewiakP. StepniakJ. Jurczak*Institute of Organic Chemistry, Polish Academy of Sciences, Poland
as
Linear Neutral Receptors for Anions: Synthesis, Structure and Applications
S
hort Review4555
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Synthesis 2018, 50, 4569–4576DOI: 10.1055/s-0037-1610305
T. Jin*L. Zhao*X. LiuL. SunJ.-F. LinZ.-B. Zheng*Chengdu University, P. R. of ChinaSichuan Institute for Food and Drug Control, P. R. of China
Recent Advances in the Total Synthesis of Clavaminols
C9H19
NH2
OH
C9H19
NHAc
OH
C9H19
NHAc
OH
HO
C9H19
NH2
OH
HO
R
NH2
OH
clavaminol BR = Z-non-5-enyl
R
NHAc
OH
clavaminol NR = i-C10H21
(–)-clavaminol A (+)-clavaminol C (+)-clavaminol H
deacetyl (+)-clavaminol H
Representative Clavaminol
Natural Products
S
hort Review4569
https://doi.org/10.1055/s-0037-1610305https://doi.org/10.1055/s-0037-1609943https://doi.org/10.1055/s-0037-1611014
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VII
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Synthesis 2018, 50, 4577–4590DOI: 10.1055/s-0037-1610250
H. OkamotoK. TohT. MochizukiH. NakatsujiA. Sakakura*M. Hatano*K. Ishihara*Nagoya University, JapanOkayama University, Japan
Syn thesis
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Chiral Pyrophosphoric Acid Catalysts for the para-Selective and Enantioselective Aza-Friedel–Crafts Reaction of Phenols
Feature
4577
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Synthesis 2018, 50, 4591–4605DOI: 10.1055/s-0037-1611065
W. SunP. TrincheraN. KurdiD. PalomasR. Crespo-OteroS. AfshinjavidF. JavidC. R. Jones*Queen Mary University of London, UK
as
Aryne-Mediated Arylation of Hantzsch Esters: Access to Highly Substituted Aryl-dihydropyridines, Aryl-tetrahydropyridines and Spiro[benzocyclobutene-1,1′-(3′,4′-dihydropyridines)]
C-2 arylation(if R = H)
C-3 arylation(if R ≠ H)
‘Hantzsch ester’
Regioselective C-2 or C-3aryne ene reaction Bioactive highly functionalizedN-heterocycles Access novel spirocyclicbenzocyclobutenes
N Me
Me
R
CO2EtEtO2C
ArN
EtO2C CO2Et
Me
H R
Me
H
HH
R1N
EtO2C CO2Et
MeMe
R
ArMe
N
CO2Et
Me
Me
R
EtO2C
Ar
arylation/spirocyclization
+
excess
R1
aryne
Feature
4591
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Synthesis 2018, 50, 4606–4610DOI: 10.1055/s-0037-1610659
D. BaidilovM. MakarovaL. RycekT. Hudlicky*Brock University, Canada
Preparation of Rearranged Allylic Isocyanates from the Reaction of Allylic Alcohols with 1-Cyano-4-dimethylaminopyridinium Bromide
OHR2
R3
R1 BrCN, DMAP
CH2Cl2, 0 °C to rtone synthetic operation
R1
R3
N
R2
CO
9 examplesup to 74% yield
PSP
4606
https://doi.org/10.1055/s-0037-1610659https://doi.org/10.1055/s-0037-1611065https://doi.org/10.1055/s-0037-1610250
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Synthesis 2018, 50, 4611–4616DOI: 10.1055/s-0037-1609554
T.-S. Jiang*Q. ZhangG. LiX. ChengY. Cai*Anhui Agricultural University, P. R. of China
Syn thesis
Syn thesis
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DDQ-Mediated Oxidation of Allylarenes: Expedient Access to Cinnamaldehyde-Containing Phenylpropanoids
R1O DDQ (2.2 equiv)H2O
R1O
CHO
OMe
O
OMe
O
CHO
· highly selective mono-oxidation· useful synthetic strategy
metal-free
· metal-free and mild conditions· useful in phenylpropanoids synthesis· gram-scale synthesis
7 examples63–76% yield
DDQ
single product, 66% yield
+
Paper
4611
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Synthesis 2018, 50, 4617–4626DOI: 10.1055/s-0037-1610252
G. ToyookaA. TujiK.-i. Fujita*Kyoto University, Japan
as
Efficient and Versatile Catalytic Systems for the N-Methylation of Primary Amines with Methanol Catalyzed by N-Heterocyclic Carbene Complexes of Iridium
Ir NH3NH3
N
N
R
R
cat. 2+
Alk NH2
Ar NH2
Ir-NHC cat.
50 to 90 °CMeOH
K2CO3
120 °C
Alk NMe
Me
Ar NMe
H
Ar NMe
Me
Ir-NHC cat.K2CO3
Ir-NHC cat.
+
MeOH+
Ir Cl
ClN
N
R
R
cat.
Paper
4617
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Synthesis 2018, 50, 4627–4636DOI: 10.1055/s-0037-1610536
Z.-H. YangJ.-N. ZhuZ.-H. JinJ. ZhengS.-Y. Zhao*Donghua University, P. R. of ChinaShanghai Institute of Organic Chemistry, P. R. of China
Copper-Catalyzed Intermolecular Thioamination of Maleimides with Thiols and Formamides: A One-Step Construction of 3-Amino-4-thio-maleimides Using Formamides as Nitrogen Sources
Unperturbed double bond
R2, R3, R4 = H, aryl, alkylR1 = aryl, alkyl
+
N OO
R2
R1S H
N OO
R2
R1SH
CuI (0.2 equiv)
HBF4, O2, 120 °C+ N
R4
R3
HN
R4
R3H
O
Direct C(sp2)–H bond difunctionalizations
High efficiency and atom economy
High functional-group tolerance
C–S and C–N bond formation in one step
Formamides as the nitrogen sources
23 examples, 27–87% yields
Paper
4627
https://doi.org/10.1055/s-0037-1610536https://doi.org/10.1055/s-0037-1610252https://doi.org/10.1055/s-0037-1609554
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Synthesis 2018, 50, 4637–4644DOI: 10.1055/s-0037-1610231
K.-J. LiuX.-L. ZengY. ZhangY. WangX.-S. XiaoH. YueM. WangZ. TangW.-M. He*Hunan University of Science and Engineering, P. R. of China
Syn thesis
Syn thesis
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Palladium-Catalyzed Reductive Coupling of Nitroarenes with Phenols leading to N-Cyclohexylanilines
+
HN
NO2R1
R1HOPd/C (10 mol%)
HCO2Na, TFAtoluene, 100 °C
R2
R2
21 examplesup to 92% yield
Paper
4637
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Synthesis 2018, 50, 4645–4650DOI: 10.1055/s-0037-1610537
Y.-Y. LiaoL. XuR.-Y. Tang*W.-X. Zheng*South China Agricultural Univer-sity, P. R. of China
as
Palladium-Catalyzed Selective Synthesis of 3-Hydroxy-2-oxindoles via Cascade C–H Cycloaddition and Oxidation of α-Aminoacetophenones
N
ON
O
HO
R1 R2
R1
R2H
MeMe
H2OPd(OAc)2 (10 mol%)
AgOAc (3 equiv)
MeCN/t-BuOH120 °C, 12 h
15 examples37–69% yields
Paper
4645
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Synthesis 2018, 50, 4651–4658DOI: 10.1055/s-0037-1610822
M.-Y. Chang*Y.-S. WuY.-T. HsiaoKaohsiung Medical University, Taiwan
Gram-Scale Synthesis of β-Sulfonyl Styrenes
1,1-diacetoxylation/deacetoxylative sulfonylation
ArArPPA, Ac2O S
O
O
ROAr
OAc
OAc
then NaSO2R
economical and gram-scale synthesis 29 examples 41–93% yields
Paper
4651
https://doi.org/10.1055/s-0037-1610822https://doi.org/10.1055/s-0037-1610537https://doi.org/10.1055/s-0037-1610231
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X
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Synthesis 2018, 50, 4659–4667DOI: 10.1055/s-0037-1610652
Y. SatoY. AshidaD. YoshitakeM. HoshinoT. TakemotoY. Tanabe*Kwansei Gakuin University, Japan
Syn thesis
Syn thesis
s st
Stereoretentive Suzuki–Miyaura and Kumada–Tamao–Corriu Cross-Couplings for Preparing (E)- and (Z)-Stereodefined, Fully Substituted α,β-Unsaturated Esters: Application for a Pharmacophore Synthesis
R1
O
R2
CO2Me
R1CO2Me
R2
OTs
R1
OTs
CO2Me
R2
R1CO2Me
R2
Ar (or R)
R1
Ar (or R)
CO2Me
R2
(E)-Enol tosylations
ArB(OH)2 [SM] or RMgBr [KTC]
(Z)-Enol tosylations
cat. Pd(OAc)2, cat. SPhos
C6H4(m-OBn)
CO2Me
Me
C6H4(m-OBn)
Me
CO2Me
Application
Paper
4659
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Synthesis 2018, 50, 4668–4682DOI: 10.1055/s-0037-1609563
G. LiuY. WuJ. HanW. HeJ. ChenH. DengM. ShaoH. Zhang*W. Cao*Shanghai University, P. R. of ChinaShanghai Institute of Organic Chemistry, P. R. of China
as
N-Heterocycle-Triggered MCRs: An Approach to the Concise Synthesis of Perfluoroalkylated Spiro-1,3-oxazines
N
RF CO2Me
N
O
O
R3
N O
NRF
MeO2C
R3
O N O
NRFMeO2C
OHH
R3MeCN
70 °C, 12 hsealed tube
R1
R2
R1 R1
R2 R2
up to 97% total yield22 examples
RF = CF3, C2F5, n-C3F7
Paper
4668
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Synthesis 2018, 50, 4683–4689DOI: 10.1055/s-0037-1609914
R. J. McKinnieT. DarweeshP. A. ZitoT. J. Shields Jr.M. L. Trudell*University of New Orleans, USA
Synthesis of the 5-Fluoro-4-hydroxypentyl Side Chain Metabolites of Synthetic Cannabinoids 5F-APINACA and CUMYL-5F-PINACA
Paper
4683
https://doi.org/10.1055/s-0037-1609914https://doi.org/10.1055/s-0037-1609563https://doi.org/10.1055/s-0037-1610652
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XI
Syn thesis
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Synthesis 2018, 50, 4690–4694DOI: 10.1055/s-0037-1610221
M. KohrU. Kazmaier*Universität des Saarlandes, Germany
Syn thesis
Syn thesis
s st
Stereoselective Synthesis of d4-(S)-Lysine from (S)-Serine
Serine
NH2
H2N COOH
DD
DD
BocHN COOMe
I
1) Zn, CuCN iodoalkyne2) D23) deprotection
45%3 steps
Paper
4690
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Errata
4695
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https://doi.org/10.1055/s-0037-1610221