Imprimatur:
Date, Signaturetc0819st.fm 4/23/19
Accounts andRapid Communications in Chemical Synthesis
2019Vol. 30, No. 8
MaySyn lett
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Synlett 2019, 30, 869–874DOI: 10.1055/s-0037-1612078
S. Rajkumar J. Wang X. Yang*ShanghaiTech University, P. R. of China
Syn lett
as
Asymmetric Transformations of α-Hydroxy Enamides Catalyzed by Chiral Brønsted Acids
NR1R2
OHR3
R4
a−hydroxyl enamide
chiral Brønsted acid
NR1R2
R3 R4
NR1R2
R4
H-X
Nucleophilic Addition
NR1R2
R4
Nu
NazarovElectrocyclization
R3
NR1R2
R4
Het/Ar1
isomerization
2-amidoallyl cation a,b-unsaturated ketiminium
H-Nu
O
OP
O
X-H
Ar
Ar
X = O or NTf
OO
Ar
Ar
PO
OHor
Chiral Brønsted Acid Catalysts:
X
X
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Synlett 2019, 30, 875–884DOI: 10.1055/s-0037-1612109
E. R. M. HabrakenA. R. JuppJ. C. Slootweg*University of Amsterdam, The Netherlands
Diazonium Salts as Nitrogen-Based Lewis Acids
Synpacts875
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Synlett 2019, 30, 885–892DOI: 10.1055/s-0037-1611696
J. TangD. ChenG. ZhangH. Yang*G. Cheng*Nanjing University of Science and Technology, P. R. of China
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A “Green” Primary Explosive: Design, Synthesis, and Testing
Account885
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Synlett 2019, 30, 893–902DOI: 10.1055/s-0037-1611705
A. Martinez-Cuezva*C. Lopez-LeonardoM. AlajarinJ. Berna*Universidad de Murcia, Spain
as
Stereocontrol in the Synthesis of β-Lactams Arising from the Interlocked Structure of Benzylfumaramide-Based Hydrogen-Bonded [2]Rotaxanes
N
X O
O
N
R
R
R
X = Me X = H
DiastereoselectiveRing–Closure
N
O
R
Ph O
N
R
RN
O
R
Ph O
N
R
R
Me
EnantioselectiveRing–Closure
1. CsOH-Promoted Cyclization2. Thermal Dethreading
Hydrogen-BondedBenzylfumaramide-Based
[2]Rotaxanes
Account
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Synlett 2019, 30, 903–909DOI: 10.1055/s-0037-1611777
T. ChenS. ChenS. Fu*S. QinB. Liu*Sichuan University, P. R. of ChinaChina Pharmaceutical Universi-ty, P. R. of China
Carbon–Oxygen Homocoupling of 2-Naphthols through Electrochemi-cal Oxidative Dearomatization
OH
Ar RVC(+) - Pt(–), 10 mA[RuCl2(p-cymene)]2 (2.5 mol%)
Ferrocene (0.2 equiv), KPF6 (2.0 equiv)H2O/1,4-dioxane (4:1), 90 °C, 4 h
O
Ar
O
ArR1
R1
16 examples, up to 92% yield
R1
RVC = reticulated vitreous carbon
Letter
903
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Synlett 2019, 30, 910–918DOI: 10.1055/s-0037-1611783
B. HuQ. ShiF. LuP. ZhangP. PengC. ZhaoY. DuH. SuS. Li*S. Pang*F. NieBeijing Institute of Technology, P. R. of China
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General and Greener Synthesis of Diverse Functional Organic Salts through Schiff Base Chemistry
H
O
+ H2N
HN NH2
NH2
NNH
NH2
NH2
+ H2O
Free of metal salts
Water sole byproduct
Abundant structures
Access to polyanion salts
mild conditions
general and greener
Broad substrate scope (>70 examples) Easy modulation
Advantages:
R1CHO eg:CHO CHO
OHCCHO
OHC
R2 eg: NN
NO2
NO2
N
N
CN
CNCOO
Yield range: 56–97%
R2
R1
R1
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Synlett 2019, 30, 919–923DOI: 10.1055/s-0037-1612416
V. Y. ShuvalovA. S. RuppA. K. KuratovaA. S. FisyukA. A. NefedovG. P. Sagitullina*F. M. Dostoevsky Omsk State University, Russian Federation
as
Synthesis of -Carbolines and the Alkaloid Quindoline through a Molybdenum-Catalyzed Cadogan Cyclization and their Photolumines-cent Properties
N
CO2Et
R1
NO2
R2 NR1
CO2Et
NH
R2
PPh3 (2.4 equiv), MoO2Cl2(DMF)2 (5 mol%)
p-cymene, D, 3–6 h
N
NO2
(CH2)n
N
(CH2)n
HN
n = 4, 6, 7, 10 R
R
R = H, Me, OMe, Cl
R1 = Me, c-Pr; R2 = H, OMe, Me 6 examples55–71% yield
16 examples40–68% yield
N
NO2
N
HN
quindoline
2 steps
Cryptolepissanguinolenta
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919
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Synlett 2019, 30, 924–927DOI: 10.1055/s-0037-1611805
D. NakajimaK. SueyoshiK. OriharaT. Teruya*S. Yokoshima*Nagoya University, JapanUniversity of Ryukyus, Japan
Synthesis of Majusculamides A and B
O
N O
O
NNH2
O
MeO
R
O
N O
O
NNH2
O
MeO
S
majusculamide A13% from L-valine
majusculamide B18% from L-valine
Letter
924
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Synlett 2019, 30, 928–931DOI: 10.1055/s-0037-1611766
R. Yuan Q. Shou Q. MahmoodG. XuX. SunJ. Wan*Q. Wang*Qingdao University of Science and Technology, P. R. of ChinaQingdao Institute of Bioenergy and Bioprocess Technology, P. R. of China
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Kinetic Studies on Guanidine-Superbase-Promoted Ring-Opening Polymerization of -Caprolactone
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Synlett 2019, 30, 932–938DOI: 10.1055/s-0037-1611780
C.-L. DuanX.-Y. LiuY.-X. TanR. DingS. Yang*P. Tian*G.-Q. Lin*Shanghai Normal University, P. R. of ChinaUniversity of Chinese Academy of Sciences, P. R. of ChinaShanghai University of Tradition-al Chinese Medicine, P. R. of China
as
Acetic Acid-Promoted Rhodium(III)-Catalyzed Hydroarylation of Terminal Alkynes
DG
H+ H R
[Cp∗RhCl2]2 (2.5 mol%)
HOAc, rt, 12 h
DG H
R
excellent regioselectivity
R = aryl, alkyl
broad substrate scope
AgSbF6 (15 mol%)(1.2 equiv)
low alkyne loading
mild reaction conditions
37 examplesup to 99% yield
Ar Ar
DG = directing groupCp* = pentamethylcyclopentadienyl
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Synlett 2019, 30, 939–942DOI: 10.1055/s-0037-1611481
C. LisT. Berg*Leipzig University, Germany
Synthesis of TRIPCO: A New Cyclooctyne for iSPAAC
NH
F3C CF3
N3
NH
F3C CF3
NN
N
TRIPCO
CD3CN, r.t.
Isomer-free SPAAC
NH
6 steps
k2 = 0.083 M–1 s–1NH
F3C CF3
NN
N
=
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939
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Synlett 2019, 30, 943–946DOI: 10.1055/s-0037-1612413
S. Koguchi*Y. ShibuyaY. IgarashiH. TakemuraTokai University, Japan
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Ionic-Liquid-Supported 1,3-Dimethylimidazolidin-2-one: Application as a Reusable Halogenation Reagent
Ionic Liquid Phase
SubstrateReaction
Ionic Liquid Phase
NNMeN
Cl
N
XCl
X = Cl , BF4 , PF6
Ionic Liquid Phase
Organic Phase
R OH
Product
R Cl
Oxalyl Chloride
6 examples, 85–99% yield
Letter
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Synlett 2019, 30, 947–950DOI: 10.1055/s-0037-1611477
W.-P. DingJ. DuX.-Y. LiuD. ChenC.-H. Ding*Q.-H. Deng*X.-L. Hou*Shanghai Normal University, P. R. of ChinaShanghai Institute of Organic Chemistry (SIOC), P. R. of ChinaShanghai University, P. R. of China
as
Palladium-Catalyzed [3+2] Cycloaddition of Vinylcyclopropane and Ketones
R1 R2
O 5.0 mol% Pd(OAc)210.0 mol% (rac)-BINAP
THF, rt O
NC
NC
NCCN
R2
R1+
R1 = aryl, alkylR2 = CF3, CO2R 30–99% yield
Letter
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Synlett 2019, 30, 951–954DOI: 10.1055/s-0037-1612427
K. MakinoY. HasegawaT. InoueK. ArakiH. TabataT. OshitariK. ItoH. NatsugariH. Takahashi*Tokyo University of Science, Japan
Chemoselective Demethylation of Methoxypyridine
N
OCH3 L-selectride(3 equiv)
THF, refluxR
N
OH
R
R = H, Cl, CH3, NH2 9 examples56–89% yield
H BLi
L-selectride
N
OCH3
S
HN
N
OCH3N
OH
S
HN
N
OCH3
L-selectride(3 equiv)
THF, reflux3 h, 94%
Chemoselectivity
Letter
951
X
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Synlett 2019, 30, 955–960DOI: 10.1055/s-0037-1611758
L.-L. Mao*L.-X. QuanX.-H. ZhuC.-B. JiA.-X. Zhou*F. ChenD.-G. ZhengShangrao Normal University, P. R. of China
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Visible-Light-Mediated Tandem Sulfonylation/Cyclization of Vinyl Azides with Sulfonyl Hydrazines for the Synthesis of 6-(Sulfonylmeth-yl)phenanthridines under Mild Conditions
+N3
R3S
O
ONHNH2 N
S
O
O
R3
TBPB, Na2CO3, MeCNBlue LEDs, rt, Ar
R2
R2
R1 R1
28 examples, up to 84%
Ru(bpy)3Cl2 6H2O
TBPB = tert-butyl peroxybenzoate
Letter
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Synlett 2019, 30, 961–966DOI: 10.1055/s-0037-1611769
T. Osako*R. KaiserK. ToriiY. Uozumi*Institute for Molecular Science (IMS) and JST-ACCEL, Japan
as
Aqueous Flow Hydroxycarbonylation of Aryl Halides Catalyzed by an Amphiphilic Polymer-Supported Palladium–Diphenylphosphine Cata-lyst
I
O O Pn
PdClPh2
PS
K2CO3 (2 equiv), H2O/CH3CN100 °C, system pressure: 5 barsolution flow rate: 1.0 mL/min
contact time: 58 s
Continuous Flow Reactor
R R
OH
O
73–99%
packed in column cartridges
CO
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Synlett 2019, 30, 967–971DOI: 10.1055/s-0037-1611790
J. BielefeldS. MannhauptM. SchmidtmannS. Doye*Universität Oldenburg, Germany
Hydroaminoalkylation of Allenes
Letter967
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Synlett 2019, 30, 972–976DOI: 10.1055/s-0037-1611802
T. Shirai*K. SugimotoM. IwasakiR. SumidaH. FujitaY. YamamotoNational Institute of Technology, Kochi College, Japan
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Decarbonylation through Aldehydic C–H Bond Cleavage by a Cationic Iridium Catalyst
HR
O
cat. Ir(I)+/xyl-BINAP
135 °CR H
15 examples28–91% yield
R = aryl, alkyl– CO
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Synlett 2019, 30, 977–981DOI: 10.1055/s-0037-1611806
N. UshidaN. NagaiM. AdachiT. Nishikawa*Nagoya University, Japan
as
Concise Stereocontrolled Synthesis of an -Carbagalactose Segment of RCAI-56, a Candidate Anticancer Agent
BnO
OHC
BnO
O
H
MacMillan catalyst
91% ee
3 steps
BnOH, NaHWX-R, DMSO
Cl
Cl OH
BnO
BnO
BnO
OBn1. nine-step synthesis2. gram scale3. highly stereoselective4. four crystalline intermediates
O
O
BnO
4 steps
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Synlett 2019, 30, 982–986DOI: 10.1055/s-0037-1611768
H. JinZ. GaoS. ZhouC. Qian*Zhejiang University, P. R. of China
One-Pot Approach for SNAr Reaction of Fluoroaromatic Compounds with Cyclopropanol
R = –NO2, –CN, –CF3, –X, –COOH, –NH2, –OCH3
10 examples 35.6–95.1% yield
Cs2CO3
OH
F O
DMFRR
Letter
982