Imprimatur: Date, Signature tc0319st-print.fm 1/28/19...Imprimatur: Date, Signature...
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Imprimatur:
Date, Signaturetc0319st-print.fm 1/28/19
Accounts andRapid Communications in Chemical Synthesis
2019Vol. 30, No. 3
FebruarySyn lett
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Synlett 2019, 30, 245–251DOI: 10.1055/s-0037-1610336
E. Haak*Otto von Guericke University Magdeburg, Germany
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Modern Annulation Strategies for the Synthesis of Cyclo[b]fused Indoles
Cascade annulation
NH
NH
NH
NH
NHR
N-Cyclization C-Cyclization
Addition
NHR NHR NHR
NR
5–7
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Synlett 2019, 30, 252–256DOI: 10.1055/s-0037-1610348
J. LangY. Wei*Southwest University, P. R. of China
Difunctionalization of the Isocyano Group: Atom-Economic Synthesis of Pyrimidinediones
+
NH
C
N
O
R
O18NO18
O
RCN
NH
C
O18
O
NR
isocyanideinsertion
Mumm-typerearrangement
difunctionalization of isocyano group
Ag
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252
VI
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ted.
Synlett 2019, 30, 257–262DOI: 10.1055/s-0037-1610338
A. MaityD. C. Powers*Texas A&M University, USA
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Hypervalent Iodine Chemistry as a Platform for Aerobic Oxidation Catalysis
II I
O
O
RO
OR
Carbonyl FunctionalizationC–H Amination
C–C Cleavage of 1,2-DiolsAlcohol Oxidation
Sub SuboxSubox Sub
Aerobic I(III) Catalysis Aerobic I(V) Catalysis
RR R
RCHO, O2 RCHO, O2
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Synlett 2019, 30, 263–274DOI: 10.1055/s-0037-1611063
B. Kräutler*University of Innsbruck, Austria
as
Chlorophyll Breakdown – How Chemistry Has Helped to Decipher a Striking Biological Enigma
Account
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Synlett 2019, 30, 275–286DOI: 10.1055/s-0037-1610303
L. SchulzS. R. Waldvogel*Johannes Gutenberg-Universität Mainz, Germany
Solvent Control in Electro-Organic Synthesis
Account275
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Synlett 2019, 30, 287–292DOI: 10.1055/s-0037-1612010
Y. Kon*T. NakashimaT. FujitaniT. MurayamaW. Ueda*National Institute of Advanced Industrial Science and Technolo-gy, Tsukuba, JapanHokkaido University, JapanKanagawa University, Japan
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Dehydrative Allylation of Amine with Allyl Alcohol by Titanium Oxide Supported Molybdenum Oxide Catalyst
reusable solid catalystTiO2
OH
OHR
NR'
H
RNH
H
dispersed MoO3
RN
R'
RN N R+
up to 98% yield14 examples
– H2O
– H2OR, R' = alkyl, aryl...
H
+
+
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Synlett 2019, 30, 293–298DOI: 10.1055/s-0037-1611706
N. MedishettiA. KaleJ. B. NanuboluK. Atmakur*Indian Institute of Chemical Technology, India
as
Molecular-Iodine-Promoted Synthesis of Dihydrobenzofuran-3,3-dicarbonitriles through a Novel Rearrangement
O
O Ar
CN
NH2
I2, Et3N
DCE, reflux, 2 h
O
O NC CN
Ar
C–C and C–O bond dissociation
Novel rearrengement
Yields up to 85%Wide substrate scope
New C–C and C–O bond formation
Scalable process18 examples
Letter
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Synlett 2019, 30, 299–302DOI: 10.1055/s-0037-1611937
V. V. Baranov*M. M. AntonovaN. G. KolotyrkinaI. E. ZaninA. N. KravchenkoRussian Academy of Sciences, Russian Federation
Direct Synthesis of 1-Alkyl-6-hydroxyalkyl-3a,6a-diphenylglycolurils from 1-Alkylimidazolinones and Their Cyclic Analogues
N
HN
O
O
Ph
PhN
HN
HN
NO O
Ph
Ph
OH
HO
Rn
**
O
HN
H2N
R N
NOH
Ph
PhO
R
NH2
NHO
HOn
4 examples(78–90%)
8 examples(74–88%)
n
R = Alk, n = 1, 2
Letter
299
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Synlett 2019, 30, 303–306DOI: 10.1055/s-0037-1611957
T. Q. Hung*N. M. QuanH. Van DongT. D. NguyenH. L. T. AnhT. Q. HungN. Van TuyenN. T. ThuanT. T. Dang*P. Langer*Vietnam Academy of Science and Technology, VietnamVietnam National University, VietnamUniversität Rostock, Germany
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Synthesis of 5-Aryl-5H-pyrido[2',1':2,3]imidazo[4,5-b]indoles by Domino Pd- and Cu-Catalyzed C–N Coupling Reactions
N
N
Br
N
N
N
O
Br
[Pd] [Cu]
Br
R
H2NR
61–76%
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Synlett 2019, 30, 307–310DOI: 10.1055/s-0037-1610859
V. TaşdemirB. KuzuM. TanH. GençN. Menges*SAFF Chemical Reagents R&D Lab. YYU-TEKNOKENT, TurkeySAFF Chemical Reagents R&D Van Yüzüneü Yil University, Turkey
as
Copper-Catalyzed Synthesis of Fused Imidazopyrazine N-Oxide Skeletons
Letter
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Synlett 2019, 30, 311–314DOI: 10.1055/s-0037-1612009
R. N. Kadikova*I. R. RamazanovO. S. MozgovoiA. M. GabdullinU. M. DzhemilevRussian Academy of Sciences, Russian Federation
2-Zincoethylzincation of 2-Alkynylamines and 1-Alkynylphosphines Catalyzed by Titanium(IV) Isopropoxide and Ethylmagnesium Bromide
R X
R
D(H)D(H)
R
II
8 examples (62–80%)
X = CH2NR'2 or PPh2R = alkyl, Ph
Et2Zn (2.5 equiv, 1 M in hexanes)Ti(O-iPr)4 (0.1 equiv, 0.5 M in hexanes)EtMgBr (0.2 equiv, 2.5 M in Et2O)
Et2O, 18 hzn
R
Xzn
D2O (H2O)
I2
NR'2 NR'2P(Q)Ph2
R
D(H)D(H)
1. D2O (H2O) 2. H2O2 (S8)
11 examples (65–88%)4 examples (55–63%)
zn = Zn1/2; ZnEt. Q = O, S.
Letter
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Synlett 2019, 30, 315–318DOI: 10.1055/s-0037-1611698
Y. MatsukawaT. Hirashita*Nagoya Institute of Technology, Japan
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Copper(I)- and Mesoionic-Hydroxyamide-Catalyzed Chemoselective Aerobic Oxidation of Primary Benzylic Alcohols
No over-oxidation
Compatible with electron-deficient substrates
Base metal systemMesoionic nitroxy catalyst
Y = CH, N
Selective for benzylic alcohols
R
OH 5 mol%
CuI (5 mol%), bpy (5 mol%), NMI (10 mol%), MeCN, air, r.t.
N
N N
N
Ph
Ph
N
OH
53–99%YX
R
O
YX
X = Cl, NO2, OMe, CO2Me
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Synlett 2019, 30, 319–324DOI: 10.1055/s-0037-1610353
Z. Wang◊
T. Song◊
Y. Yang*Chinese Academy of Sciences, P. R. of China
as
Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon
Letter
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Synlett 2019, 30, 325–328DOI: 10.1055/s-0037-1611975
S.-k. A. DaleyN. K. Downer-Riley*Department of Chemistry, The University of the West Indies, Jamaica
An Improved Synthesis of Balsaminone A
Letter325
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Synlett 2019, 30, 329–332DOI: 10.1055/s-0037-1611183
T. GuoY. GaoZ. Li*J. LiuK. Guo*Nahjing Tech University, P. R. of China
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Cyclopropenium-Activated DMSO for Swern-Type Oxidation
OHR
R'
OR
R'
scalable (>1 g) operationally simpleup to 24 substrates recyclable by-product
(up to 93% yield)S Ph Ph
ClCl
activatorprimary &
secondary alcoholsR = aliphatic, aromatic, (hetero)aryl
S
O
R' = H, aliphatic, aromatic
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Synlett 2019, 30, 333–337DOI: 10.1055/s-0037-1611958
Y. SuganumaY. Kobayashi*Tokyo Institute of Technology, Japan
as
Formation of COOH-Ylides, and Their Reactivities and Selectivities in Wittig Reactions
Alk-CHO
CH
Ph3P+
carboxy ylides
(hitherto unexplored ylides)
COOH–
CCO2H
H
C
H
Alk
Z-olefins
CH
HBr– Ph3P+ COOH
NaHDMS
1 equiv
Letter
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Synlett 2019, 30, 338–342DOI: 10.1055/s-0037-1611976
Y. SuganumaS. SaitoY. Kobayashi*Tokyo Institute of Technology, Japan
Synthesis of 8-HEPE and 10-HDoHE in both (R)- and (S)-Forms via Wittig Reactions with COOH-Ylides
CO2HBr– Ph3P+
OTBS
CHO*
Ph3P OH
*
NaN(TMS)2(1 equiv per Wittig reagent)
+–
THF/HMPA
(R)- and (S)-enantiomer
Bu4NF
CO2H (not CO2–)
CO2H
(8R)- and (8S)-HEPE
OH
CO2H*(10R)- and (10S)-HDoHE
Similarly,
(carboxy ylide)
Letter
338
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Synlett 2019, 30, 343–347DOI: 10.1055/s-0037-1612011
S. Hong*Y. LuM. MoritaS. SaitoY. KobayashiB. JunN. G. BazanX. XuY. WangLouisiana State University Health Sciences Center, USA
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Stereoselective Synthesis of Maresin-Like Lipid Mediators
TMS
O
OTBSOTBS *
OH
CO2H
OH
**
*Organic
Synthesis
ChiralLC-MS/MS
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Synlett 2019, 30, 348–352DOI: 10.055/s-0037-1611461
J. WuL. BishopJ. GuoZ. Guo*Case Western Reserve Universi-ty, USAUniversity of Florida, USA
as
An Investigation of the Reactions between Azido Alcohols and Phosphoramidites
OH
N3 iPr2N P
OBn
OBn
O
N3
POBn
OBn
O
NH
P
OBn
OCn=3–5 Cn=3–5
intramolecularStaudinger
reaction
tetrazole, toluene80 °C, 2 h
Cn=3–5
40–65%
Cn=3–5 = O
(literature)
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Synlett 2019, 30, 353–355DOI: 10.1055/s-0037-1611462
S. WangG. A. Kraus*Iowa State University, USA
Annulations of 5-Phenylthiobutenolides and First Synthesis of (±)-Indanostatin
OH
OH
CO2Me
OO
SPh
CO2Me
Hauser–Kraus annulation
OH
OH
O
OOOH
indanostatin
Letter
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Synlett 2019, 30, 356–360DOI: 10.1055/s-0037-1611694
M. RamasamyH.-C. LinS.-C. KuoM.-T. Hsieh*School of Pharmacy, China Medi-cal University, Taiwan
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Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones
OH
Ar
Ar
O
RF2
R1RF
2
R1 BF3·OEt2 (0.5 equiv)
DCE, heat
orAr
O
OH
RF2 R1
R1 = H, CH3, C2H5, n-C4H9 RF
2 = CF3, C2F5, o-ClPhCF2, o-CF3PhCF2
R1 = Ph, p-ClPhRF
2 = CF3
18 examples36–86% yield
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