Imprimatur:

Date, Signaturetc1618st.fm 9/21/18

Accounts andRapid Communications in Chemical Synthesis

2018Vol. 29, No. 16

Oktober ISyn lett

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Synlett 2018, 29, 2081–2086DOI: 10.1055/s-0037-1610161

J. K. VandavasiS. G. Newman*University of Ottawa, Canada

Syn lett

as

A High-Throughput Approach to Discovery: Heck-Type Reactivity with Aldehydes

R

O

HR'

X+R

O

R'

conditions

Ni(cod)2Triphos

TMP

Metal?

Ligand?

(Pseudo)halide?

Base?

OTf

carbonyl-Heck reaction

HTE

Synpacts

2081

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Synlett 2018, 29, 2087–2092DOI: 10.1055/s-0037-1610025

G. Chen*Y. YuX. Huang*Dongguan University of Technol-ogy, P. R. of ChinaFujian Institute of Research on the Structure of Matter, P. R. of China

Palladium-Catalyzed Annulation via Acyl C–H Bond Activation

H

O

X

R1

R2

R1

R2

O

Pd

Ph CO2R8

N2

X = Cl, Br, I

OO

Ph

OR8

R6

O

R5

R4R3

O

O

Ar Ar

ArAr

Ar

Ar

Ar

Acyl C-H Bond Cleavage

Synpacts

2087

Imprimaturhttps://doi.org/10.1055/s-0037-1610025https://doi.org/10.1055/s-0037-1610161

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Synlett 2018, 29, 2093–2107DOI: 10.1055/s-0037-1610531

Y. Kuninobu*Kyushu University, Japan

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Development of Novel C–H Bond Transformations and Their Application to the Synthesis of Organic Functional Molecules

N

N

O

N

N

O

n

R

R

C–H Transformations

Regiocontrol Trifluoromethylation Organic functional materials

N

N

Ir NR2

O

N N

O

H H hydrogenbonds

N

MeO

HON

CF3

H

Account

2093

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Synlett 2018, 29, 2108–2116DOI: 10.1055/s-0037-1609627

M. BarbazangesL. Fensterbank*Sorbonne Université, France

as

The Invention of New Methodologies: An Opportunity for Dating Nat-ural Products

N

N

O

a-methyldeoxyvasicinone capnellene

H H

MeHCO2HHO2C (2S,3R)-(+)-roccellic acid

CO2HHO2C

(2R,3R)-(+)-sphaeric acid

HO

OH

epi-valeneomerin B

AcOO

sabina ketone

SO

O

passion fruit aroma

Au S SO O

p-Tolp-Tol

Account

2108

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Synlett 2018, 29, 2117–2119DOI: 10.1055/s-0037-1610998

Cover Page: Atropisomerism – In Memoriam Kurt Mislow

Cluster

2117

https://doi.org/https://doi.org/10.1055/s-0037-1609627https://doi.org/10.1055/s-0037-1610531

VII

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Synlett 2018, 29, 2120–2121DOI: 10.1055/s-0037-1610998

J. S. Siegel*Tianjin University, P. R. of China

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Cluster Preface: Atropisomerism

Cluster

2120

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Synlett 2018, 29, 2122–2125DOI: 10.1055/s-0037-1610908

J. S. Siegel*Tianjin University, P. R. of China

as

Prologue: Atropisomerism

HO2C

HO2C NO2

NO2 NO2

NO2HO2C

HO2C

Cluster

2122

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Synlett 2018, 29, 2126–2130DOI: 10.1055/s-0037-1610110

M. MatsuokaA. IidaO. Kitagawa*Shibaura Institute of Technolo-gy, Japan

α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho-Substituted Phenyl Groups: Relation between Diastereo-selectivity and the ortho-Substituent

N

N

C2H5

O X

N

N

O X

Me

R

X = F, Cl, Me, Br, Et, I, i-Pr, CF3

diastereoselectivitylow high

12 examples (85–98%)

axial chirality

central chirality

axial chirality

1) LiHMDS2) R-Y

THF, –20 °C

Cluster

2126

https://doi.org/10.1055/s-0037-1610110https://doi.org/10.1055/s-0037-1610908https://doi.org/10.1055/s-0037-1610998

VIII

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Synlett 2018, 29, 2131–2136DOI: 10.1055/s-0037-1610207

C. NiM. WangL. You*Fujian Institute of Research on the Structure of Matter, P. R. of China

Syn lett

Syn lett

s st

Dynamic Covalent Chemistry within Biphenyl Scaffolds: Effects from Endocyclic to Exocyclic Sulfonamides

Cluster

2131

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Synlett 2018, 29, 2137–2140DOI: 10.1055/s-0037-1609869

S. Toyota*T. SaibaraK. FujiseT. OkiT. IwanagaTokyo Institute of Technology, Japan

as

Synthesis and Conformational Analysis of 10-Mesitylanthracene-1,8-diyl Oligomers

Mes

Br Br Ni(cod)2bipy, cod

MesMes

Mes

n–2

oligomerization

StructureConformation

tolueneDMF

7.7–10.2% n = 2–4

Cluster

2137

Thi

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Synlett 2018, 29, 2141–2146DOI: 10.1055/s-0037-1609868

H. Tabata*Y. TsujiT. YonedaT. TasakaT. OshitariH. Takahashi*H. Natsugari*Teikyo University, JapanAffinity Science Corporation, JapanTokyo University of Science, Japan

Atropisomerism in the 2,3,4,5-Tetrahydro-1H-1,5-benzodiazepine Nucleus: Effects of Central Chirality at C3 on the N-Mesylation Reaction

CH3SO2Cl base

boat-like

CH3SO2ClN

N

3

A

B

N

N6

3

ps.eq.

ps.eq.

chair-like

boat-like

aS*

S*

aR*

S*

N

HN

HH

H

HH

36

from less hindered side

convex

concave

thermodynamic

kinetic

6

H3CSO2

H3CSO2

5

5

Cluster

2141

https://doi.org/10.1055/s-0037-1609868https://doi.org/10.1055/s-0037-1609869https://doi.org/10.1055/s-0037-1610207

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Synlett 2018, 29, 2147–2154DOI: 10.1055/s-0037-1610190

Y. IshigakiT. IwaiY. HayashiA. NagakiR. KatoonoK. FujiwaraJ.-i. YoshidaT. Suzuki*Hokkaido University, Japan

Syn lett

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Transmission of Point Chirality to Axial Chirality for Strong Circular Dichroism in Triarylmethylium-o,o-dimers

Cluster

2147

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Synlett 2018, 29, 2155–2160DOI: 10.1055/s-0037-1609581

A. N. DinhR. R. NoorbeheshtS. T. ToenjesA. C. JacksonM. A. SaputraS. M. MaddoxJ. L. Gustafson*San Diego State University, USA

as

Toward a Catalytic Atroposelective Synthesis of Diaryl Ethers Through C(sp2)–H Alkylation with Nitroalkanes

O

O

O R1

R2 Cat. C2 (10 mol %)Cs2CO3 (10 equiv)NO2Me (10 equiv)0.1 M PhMe, 36 h

- Up to 80% yield- Up to 85:15 er

99:1 via trituration

H O

O

O R1

R2

Me

NH

N

O

NH

O NH

CF3

CF3

Br

Cat. C2

6 examples

Cluster

2155

Thi

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Synlett 2018, 29, 2161–2166DOI: 10.1055/s-0037-1609908

A. PaganoE. MarottaA. MazzantiG. Petrillo*C. TavaniM. Mancinelli*University of Bologna, ItalyUniversity of Genova, Italy

Stereodynamic Analysis of New Atropisomeric 4,7-Di(naphthalen-1-yl)-5,6-dinitro-1H-indoles

Cluster

2161

https://doi.org/10.1055/s-0037-1609908https://doi.org/10.1055/s-0037-1609581https://doi.org/10.1055/s-0037-1610190

X

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Synlett 2018, 29, 2167–2170DOI: 10.1055/s-0037-1610635

Y. Nagata*Y. ShimadaT. NishikawaR. TakedaM. UnoT. Ogoshi*M. Suginome*Kyoto University, JapanKanazawa University, Japan

Syn lett

Syn lett

s st

A Planar-Chiral Pillar[5]arene-Based Monophosphine Ligand with Induced Chirality at the Biaryl Axis

Cluster

2167

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Synlett 2018, 29, 2171–2175DOI: 10.1055/s-0037-1610551

B. MátravölgyiS. DeákZ. ErdélyiT. HergertP. Ábrányi-BaloghF. Faigl*Budapest University of Technol-ogy and Economics, Hungary

as

Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions

+ Et2ZnH

O

N

F3COH

N

F3C

NR1R2

OH

ArAr

ArAr

NR1R2

5%

5%

or the regioisomer H

EtOH

ee up to 96%

Cluster

2171

Thi

s do

cum

ent w

Synlett 2018, 29, 2176–2180DOI: 10.1055/s-0037-1610233

C. FischerC. Sparr*University of Basel, Switzerland

Configurationally Stable Atropisomeric Acridinium Fluorophores

Cluster

2176

https://doi.org/10.1055/s-0037-1610233https://doi.org/10.1055/s-0037-1610551https://doi.org/10.1055/s-0037-1610635

XI

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Synlett 2018, 29, 2181–2184DOI: 10.1055/s-0037-1610630

H. ZouC. HuK. ChenG. XiaoX. Peng*Nanjing University of Science and Technology, P. R. of China

Syn lett

Syn lett

s st

Cobalt Vanadium Oxide Supported on Reduced Graphene Oxide for the Oxidation of Styrene Derivatives to Aldehydes with Hydrogen Per-oxide as Oxidant

OO

CoV/rGO

R1R2 R1 O

catalyst (0.02 g), 65 °C, MeCN (5 mL)

H2O2 (30 wt%, 3 equiv), 6 h recyclable metal complexoxide catalyst

up to 96% yield

16 examples

R1 = aryl

R2 = H, NO2, Ph

Letter

2181

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Synlett 2018, 29, 2185–2190DOI: 10.1055/s-0037-1610272

J. NandiM. L. WitkoN. E. Leadbeater*University of Connecticut, USA

as

Combining Oxoammonium Cation Mediated Oxidation and Photo-re-dox Catalysis for the Conversion of Aldehydes into Nitriles

Letter

2185

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Synlett 2018, 29, 2191–2194DOI: 10.1055/s-0037-1610653

S. GaoY. MaW. ChenJ. Luo*Ningbo University, P. R. of China

Pd-Catalyzed Oxidation of Aldimines to Amides

Pd(OAc)2, TBHP

21 examplesup to 85% yield

N

R2

R1

NH

R2

R1

O

R1 = Br, Cl, F, Me, NO2R2 = CF3, NO2, COMe, Br, Cl, F, Me, t-Bu, OCF3, OMe

Letter

2191

https://doi.org/10.1055/s-0037-1610653https://doi.org/10.1055/s-0037-1610272https://doi.org/10.1055/s-0037-1610630

XII

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Synlett 2018, 29, 2195–2198DOI: 10.1055/s-0037-1610245

N. N. LeA. M. RodriguezJ. R. AlleynM. R. Gesinski*Southwestern University, USA

Syn lett

Syn lett

s st

Synthesis of 1,4-Diketones via Titanium-Mediated Reductive Homocoupling of -Haloketones

RX

O RX

O R

O

R

O

+

Ti(OiPr)4 + EtMgBr

"Ti(OiPr)3"

11 examples22–90%

R = aryl or heteroaromaticX = Cl or Br

Letter

2195

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Synlett 2018, 29, 2199–2202DOI: 10.1055/s-0037-1610234

Z.-G. XuY. DingJ.-P. MengD.-Y. TangY. LiJ. LeiC. Xu*Z.-Z. Chen*Chongqing University of Arts and Sciences, P. R. of ChinaUniversity of Electronic Science and Technology of China, P. R. of China

as

Facile Construction of Hydantoin Scaffolds via a Post-Ugi Cascade Re-action

R1 NH2

COOH

R3 N

O

N

R2

R1

O

R2 CHO R3 N

(2) K2CO3, CH3CN MW, 100 °C, 10 min

(1) MeOH, r.t. without purification

17 examples, yield 42–77%Two steps and one purificationShort reaction times

Atom economyMicrowave irradiation

One-pot protocol

leaving group

R1 = Ar

R2 = Ar

R3 = Ar, Alkyl

Letter

2199

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Synlett 2018, 29, 2203–2207DOI: 10.1055/s-0037-1609623

S. WangY. YuJ. Wen*X. Zhang*Southern University of Science and Technology, P. R. of China

Iridium/f-Amphox-Catalyzed Asymmetric Hydrogenation of Styrylglyoxylamides

[Ir(COD)Cl]2 (0.05 mol%)L1 (0.11 mol%)

O

N

HN

FePh2P

L1 f-amphox

OHN

O

R2R1

HN

O

OH

R2R1

DCE, KOHH2 (20 atm)

r.t., 12 h

NO

COOH

NH

O

Obenzazepril

TON up to 10000

16 examples96–99% yield94–98% ee

Letter

2203

https://doi.org/10.1055/s-0037-1609623https://doi.org/10.1055/s-0037-1610234https://doi.org/10.1055/s-0037-1610245

XIII

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Synlett 2018, 29, 2208–2212DOI: 10.1055/s-0037-1610247

S. NandyA. GhatakA. K. DasS. Bhar*Jadavpur University, India

Syn lett

Syn lett

s st

Chemoselective and Metal-Free Synthesis of Aryl Esters from the Cor-responding Benzylic Alcohols in Aqueous Medium Using TBHP/TBAI as an Efficient Catalytic System

tBuOOH (2 mol equiv)(Bu)4N+I– (20 mol%)

Imidazole (2 mol equiv)MeOH H2O, 8 h, 80 °C

COOMe

OOH

(86%)

OOH

(88%)

Me O R OH

OOH

tBuOOH (2 mol equiv)(Bu)4N+I– (20 mol%)

Imidazole (2 mol equiv)H2O, 8 h, 80 °C

R = MeR = H

Letter

2208

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https://doi.org/10.1055/s-0037-1610247