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

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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

Synpacts

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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

Synpacts

875

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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

Account

885

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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

893

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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

Letter

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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

Letter

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

Letter

928

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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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932

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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

=

Letter

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

947

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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

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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

Letter

961

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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

Letter

967

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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

Letter

972

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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

Letter

977

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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