Archive for the 'Synlett' Category

N,N′-Dimethyl Urea

Synlett
DOI: 10.1055/s-0029-1219573

© Georg Thieme Verlag
Stuttgart ˙ New York

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Benzyltriphenylphosphonium Peroxymonosulfate

Synlett
DOI: 10.1055/s-0029-1219570

© Georg Thieme Verlag
Stuttgart ˙ New York

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The First One-Pot Synthesis of Morita-Baylis-Hillman Adducts Starting Directly from Alcohols

Synlett
DOI: 10.1055/s-0029-1219577

Abstract

The first example of one-pot oxidative carbon-carbon bond
formation via the Morita-Baylis-Hillman reaction
using alcohols is reported. The protocol involves silica gel-DABCO
catalyzed oxidation of alcohols to aldehydes with chloramine-T followed
by their Morita-Baylis-Hillman reaction with acrylonitrile
or methyl acrylate to give 70-87% overall yields
of the corresponding ­Morita-Baylis-Hillman
adducts. The present work opens up a new and efficient synthetic
route to Morita-Baylis-Hillman adducts directly
from alcohols in a one-pot operation.
[...]

© Georg Thieme Verlag
Stuttgart ˙ New York

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New Electrophilic Bromodifluoromethylation and Pentafluoroethylation Reagents

Synlett
DOI: 10.1055/s-0029-1219579

Abstract

-(fluoroalkyl)diphenylsulfonium salts
have been successfully synthesized from the reaction between fluoroalkylsul­finates
and triflic anhydride in dichloromethane through a one-pot procedure.
These (fluoroalkyl)diphenylsulfonium
salts have been demonstrated to be effective reagents to fluoroalkylate
C-nucleophilic substrates. Ionic substitution and radical or halogenophilic mechanism
might be all involved in the reactions.
[...]

© Georg Thieme Verlag
Stuttgart ˙ New York

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Synthesis of N-Arylisoindolin-1-ones via Pd-Catalyzed Intramolecular Decarbonylative Coupling of N-(2-Bromobenzyl)oxanilic Acid Phenyl Esters

Synlett
DOI: 10.1055/s-0029-1219580

Abstract

Ethyl and phenyl oxanilates were readily prepared from -(2-bromobenzyl)anilines and oxalyl
chloride monoethyl and monophenyl esters, respectively. It was found
that the ethyl oxanilate survived in the presence of KCO in
DMA at 120 ˚C and underwent an intramolecular direct arylation
using Pd(OAc)-dppf, furnishing the 5,6-dihydrophenanthridine
derivative. In contrast, the corresponding phenyl oxanilates decomposed
upon exposure to KCO in DMA at 120 ˚C
and were transformed into -arylisoindolin-1-ones
via Pd(OAc)-dppf-catalyzed intramolecular decarbonylative
coupling. Except for the 4-methoxy-substituted oxanilic acid phenyl
ester, other phenyl oxanilates possessing electron-withdrawing (NO,
Cl) and weak electron-donating (Me) substituents provided the -arylisoindolin-1-ones in 43-80% yields.
[...]

© Georg Thieme Verlag
Stuttgart ˙ New York

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Metal-Free One-Pot Conversion of Electron-Rich Aromatics into Aromatic Nitriles

Synlett
DOI: 10.1055/s-0029-1219575

Abstract

Various electron-rich aromatics could be smoothly converted into
the corresponding aromatic nitriles in good to moderate yields by
treatment of electron-rich aromatics with POCl and DMF,
followed by treatment with molecular iodine in aqueous ammonia.
The present reaction is a novel metal-free one-pot method for the
preparation of aromatic nitriles from electron-rich aromatics.
[...]

© Georg Thieme Verlag
Stuttgart ˙ New York

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Highly Enantioselective and Regioselective Conjugate Addition of Nitromethane to 1,5-Diarylpenta-2,4-dien-1-ones Using Bifunctional Cinchona Organocatalysts

Synlett
DOI: 10.1055/s-0029-1219576

Abstract

A general and efficient asymmetric organocatalytic 1,4-Michael
addition of nitromethane to 1,5-diarylpenta-2,4-dien-1-ones (cinnamylideneacetophenones)
catalyzed by 9-thiourea-9-(deoxy)–hydroquinine
has been developed. The reactions afforded excellent enantioselectivities
(up to 99%), high yields (up to 97%), and exclusive
regioselectivity.
[...]

© Georg Thieme Verlag
Stuttgart ˙ New York

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A Practical Synthesis of (S)-Cyclopent-2-enol

Synlett null; null: 840-840
DOI: 10.1055/s-0029-1219555

© Georg Thieme Verlag
Stuttgart ˙ New York

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Chemistry of Lactam-Derived Vinyl Phosphates: Stereoselective Synthesis of (+)-Fagomine

Synlett null; null: 839-839
DOI: 10.1055/s-0029-1219556

© Georg Thieme Verlag
Stuttgart ˙ New York

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An Efficient and Short Synthesis of 4-Aryl-3-methyltetrahydroquinolines from N-Benzylanilines and Propenylbenzenes through Cationic Imino Diels-Alder Reactions

Synlett
DOI: 10.1055/s-0029-1219571

Abstract

A new, simple protocol for the BF˙OEt-catalyzed
synthesis of diverse 3-methyl-4-aryl-1,2,3,4-tetrahydroquinolines ­using
easily available starting materials and renewable phenylpropenoid
reagents is described. These compounds could serve as interesting
models in pharmacological studies.
[...]

© Georg Thieme Verlag
Stuttgart ˙ New York

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