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

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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

Synpacts

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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

Account

275

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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

+

+

Letter

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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%

Letter

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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

311

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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

Letter

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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

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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

Letter

325

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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

Letter

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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

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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

353

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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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