Letters in Organic Chemistry

ISSN: 1570-1786

Letters in Organic Chemistry
Volume 3, Number 9, September 2006

An Unusual and Stereoselective Michael Addition of α-Amino Ester- Derived N-Lithiated Azomethine Ylides Pp. 648-653

Adrien Soret, Luis Blanco & Sandrine Deloisy N-Lithiated azomethine ylides generated from N-arylidene-α-amino esters react on their Cγ-atom with a 7-oxabicyclo[2.2.1] heptadiene derived diester to yield β-amino diesters after acidic work-up.

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A One-Step Synthesis of a Carbasugar Via a Wittig Horner/Mitsunobu/Michaël Triple-Tandem Mechanism Pp. 654-657

Antoine Bussière, Véronique Barragan-Montero, Caroline Clavel, Loïc Toupet & Jean-Louis Montero An one-step methodology for the synthesis of carbasugar, involving tandem Wittig-Horner, Mitsunobu, and Michael mechanisms, is disclosed. The strategy involves CMMP and allows a quick access to a new variety of carbasugar derivatives.

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Magnesium Perchlorate: Highly Efficient and Versatile Catalyst for the Ferrier Glycosylation Reaction Pp. 658-663

Vinod T. Kamble, Babasaheb P. Bandgar, Chandrahas N. Khobragade, Rajesh N. Gacche & Vilas A. Kamble Magnesium perchlorate catalyzed preparation of 2,3-unsaturated glycosides, glycosyl azides, allyl glycosides, glycosyl cyanides is described.

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Unexpected Performance of Solid Alkaline Metal Hydroxides in Liquid Phase Oxidation of 1-Phenylethanol Pp. 664-667

Kfir Ben-Harush, Adi Wolfson & Moti Herskowitz Solis alkaline metal hydroxides displayed activity in alcohol oxidation in non-polar medium. Both organic molecules and molecular oxygen were employed as oxidants. The activity was in order KOH>NaOH>>LiOH.

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A Facile Two-Step Chemo-Enzymatic Synthesis of GDP-Mannose Pp. 668-669

Gang-Liang Huang, Xiang Liu, Hou-Cheng Zhang, Peng-George Wang Mannose is selectively converted into mannose-1-phosphate (Man-1-P, 1) without protection of the other hydroxyl groups by phosphorylation of the anomeric hydroxyl in dry tetrahydrofuran (THF) containing phosphoric acid. 1 is activated with GTP and recombinant GDP-mannose pyrophosphorylase (GDP-Man PP) to give GDP-Man 2.

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Alder-Ene Reaction of 3-Methyl-3-Cyanocyclopropene with Monoterpenes Pp. 670-673

Roman V. Ashirov, Alsu A. Balandina, Sergey V. Kharlamov, Svetlana A. Appolonova, Bruno Figadere, Shamil K. Latypov & Vitali V. Plemenkov The reaction with hindered ene-components is highly diastereoselective and provides the exo-syn product as the major adduct.

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Synthesis of AB2-Functionalized Triphenylene Derivatives Pp. 674-678

Jeonghee Kang, Degang Wang, Bagui Mahuya, Sanjiban Chakraborty & Zhonghua Peng A number of AB2-functionalized triphenylene derivatives have been synthesized through a convenient approach.

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Investigation on the Biocatalytic Oligomerization of Glycidol Pp. 679-684

Christine Schütz, Torsten Dwars & Udo Kragl Investigations on the enzymatic polymerization of glycidol are reported. The active site of enzymes is possibly not the crucial unit for the catalytic activity in this reaction.

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Organic Radical Crystals Based on TEMPO-Substituted Anthraquinones Pp. 685-688

Mitsunori Nobusawa, Hiroki Akutsu, Jun-ichi Yamada & Nakatsuji A couple of TEMPO-substituted anthraquinone isomers showed marked difference of solvating property and the resulting magnetic behavior.

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A Study of Thermal Activation of N-Nitrosoamides Pp. 689-698

Ron W. Darbeau, Edson V. Perez & Martin Brantley Mechanism of N-nitrosoamide thermolysis showing rate-determining formation of an oxadiazetyl moiety as the first step.

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Transformations of 2-(α-Furyl)- 4-(2-Oxopyrrolidinyl-1)-1,2,3,4 Tetrahydroquinolines, Cycloadducts of the Imino Diels-Alder Reaction: A Simple Synthesis of New Quinoline Derivatives Pp. 699-702

Vladímir V. Kouznetsov & Uriel Mora Cruz An efficient and simple synthesis of biologically important C-2 α-furyl substituted quinolines and isoindolo[2,1-a]quinolines using the same 2-(α-furyl)-4-(2-oxopyrrolidinyl-1)-1,2,3,4-tetrahydroquinolines prepared by imino Diels-Alder reaction was reported.

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Diels-Alder Reactions of Pyrimidine o-Quinodimethanes: Stereochemistry and Applications to the Synthesis of Tetrahydro- and Quinazoline Derivatives Pp. 703-708

Antonio Herrera, Roberto Martínez-Alvarez, Mourad Chioua, Rachid Chioua, John Almy & Angel Sánchez The reaction of the 2,4-diphenylcyclobutapyrimidine with different dienophiles leads to the formation of a variety of tetrahydro- and quinazoline derivatives.

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An Efficient Route to Thieno[2,3-d]pyrimidine Derivatives by Tandem [2,3] and [3,3] Sigmatropic Rearrangement Pp. 709-711

Krishna C. Majumdar, Nilasish Pal & Sudip K. Chattopadhyay Synthesis of biologically important novel thieno[2,3-d]pyrimidine derivatives by tandem rearrangement protocol has been developed.

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Microwave Assisted One Pot Synthesis of New Bis-Imidazolyl Indoles Pp. 712-714

Anu Agarwal, Sharad Porwal & Prem M.S. Chauhan A library of 12 bis-imidazolyl indoles have been synthesized in high yields (84-95%) using microwave irradiation.

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Synthesis of Tricyclic Pyrazolo[1,5-a]pyrimidin-7(4H)-ones Featuring Regioselective Formation of the Core Structure Pp. 715-719

Vladislav Z. Parchinsky, Olga Ushakova, Dmitry V. Kravchenko & Mikhail Krasavin The synthetic method developed features regioselective construction of the core tricyclic molecular scaffold and a remarkable case of convenient and high-yielding p-methoxybenzyl group removal from a secondary aliphatic amine that is suitable for parallel reaction arrays.

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Competitive Deprotonation in Vicinal O=SCH2CH2P=O Moieties Pp. 720-722

Nina K. Gusarova,a, Nataliya A. Chernysheva, Svetlana N. Arbuzova, Maria V. Bogdanova, Svetlana F. Malysheva, Nataliya A. Belogorlova, Igor A. Ushakov, Nadezhda M. Vitkovskaya, b, Vladimir B. Kobychev & Boris A. Trofimov Diphenyl[2-(phenylsulfinyl)ethyl]phosphine oxide readily accessible from diphenylphosphine oxide and phenyl vinyl sulfoxide reacts with sodium amide to form diphenyl(vinyl)phosphine oxide in good yield. The reaction involves generation of phosphoryl-stabilized carbanions which further eliminate benzene sulfenate anions. The preferred formation of phosphoryl-stabilized carbanions in the vicinal O=SCH2CH2P=O moiety is supported by quantum chemical calculations.

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