B. Kasenova 2

2. “Chiral” Organic Chemistry: Poster presentation P-263 ASYMMETRICAL HYDRO-,

HYDROTIOPHOSPHORUS COMPOUNDS AND SOME THEIR FUNCTIONALLY SUBSTITUTED

DERIVATIVES

1 - Kokshetau State University of S.Ualihanov, Kokshetau, Kazakhstan

2 - Saint-Petersburg State Institute of Technology (Technical University), St.-Petersburg, Russia

O.A. Aimakov¹ J.V. Oleynikova²

2. “Chiral” Organic Chemistry: Poster presentation P-264 NEW PICOLYLAMINE TEMPLATE ORGANO- CATALYST FOR ENANTIOSELECTIVE ALDOL

REACTIONS 1 - University of Malakand, Pakistan

2 - Jacobs University Bremen, Germany M. Naveed Umar^1,2

Thomas Nugent²

Ahtaram Bibi² onv@ioc.ac.ru

Picolylamine template organocatalyst containing only one stereogenic center has been identified for fast aldol reactions (16–48 h). Using 2–5 mol% of (R)- or (S)-PicAm-2, cyclohexanone (3.3 equiv) readily undergoes aldol reactions with o-, m-, and p-substituted aromatic aldehyde partners (limiting reagent), including the poor electrophile 4-methylbenzaldehyde (95–99% ee). Furthermore, functionalized cyclic ketone substrates have been converted into four aldol products 9–12 using the lowest catalyst loading (5.0 mol%) to date with the highest yield and enantioselectivity.

N

NH₂

N

NH₂

Ph Ph

2-picolylamine: promising

new organocatalyst template aldol organocatalyst example

PicAm-2

Section 3.

Advanced Methods of

Organic Synthesis

Ecopharm company was founded in 1996 by a group of chemists had been working in the field of science for a long time. The goal of our enterprise establishing is complex task solution in laboratories equipping.

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Our company sets up and completes the production with the newest most technologically advanced equipment.

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OHAUS- Japan (scales), SHIMADZU - Japan (the widest range of analytical equipment), SARTORIUS – Germany (laboratory equipment), IMPLEN – Germany (spectrophotometers of a new generation with patented technology "drop sampling”), SHINKO – Japan (weighing equipment), METTLER TOLEDO – Switzerland (scales, pH meters, analytical instrumentation for thermal analysis, titrators, electrochemical equipment, laboratory), DAIHAN – Korea (laboratory equipment), ULAB – Germany (advanced laboratory equipment), J.T. Baker – Netherlands-USA (chemicals of high purity, pharmacopoeial standards and polietilenglikolievye basics), RHEOTEST – Germany (viscometers and rheometers rotamers), HAIER – Germany (biochemical equipment),TRILOGICA – Germany (viscometers, rheometers, moisture analyzers, dilatomery, bursting machines, laboratory equipment), HUBER – Germany (the widest range of thermostats), LEKI – China (scales and spectrophotometers), SNOL-THERM – Russia (muffle, tube, tube furnaces, ovens), CEMICO – Russia (electrochemical devices), ESCO – Singapore (chemical and bioreactors), INFRASPAK-ANALYT – Russia (electrochemical devices), UNICO – (spectrophotometers), LUMEX»

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3. Advanced Methods of Organic Synthesis: Plenary lecture PL-5 THE PREPARATION OF FUNCTIONAL N-HETEROCYCLES AND THEIR APPLICATION IN

MATERIALS CHEMISTRY

University of York, Department of Chemistry, Heslington, UK D.W. Bruce duncan.bruce@york.ac.uk

Materials chemistry studies the collective behaviour of compounds that display useful properties based on responses not related to chemical reactivity, rather that depend upon, for example, electronic structure, optical and magnetic response, and photophysics.

Nitrogen heterocycles are of interest in this regard as, for instance, the nitrogen centre can perturb the electronic structure of conjugated aromatic systems, or can act as a Lewis base to facilitate interactions such as hydrogen bonding or metal coordination.

a) 4-Alkoxystilbazoles form halogen bonds to electron-poor halides such as iodine found in highly fluorinated materials, and complexes between such stilbazoles and iodopentafluoro-benzene have been characterised crystallographically. Depending on the alkoxy chain length, these complexes show liquid crystal properties and the lecture will describe systematic studies both of the halogen bond strength and of structure/property relationships, with analogies being made to related hydrogen- bonded systems.

b) Substituted phenylpyridines are classically prepared using metal-catalysed cross- coupling methodologies, but they may also be obtained using the Boger reaction, an inverse electron demand Diels-Alder reaction for which key starting compounds are 1,2,4-triazines. This chemistry may be used to prepared 1,3-(2-pyridin-2-yl)benzenes, whose platinum(II) complexes are promising, efficient chromophores for application in Organic Light-Emitting Diodes (OLEDs). Similarly, the same chemistry can lead to 2,5-diphenylpyridines whose platinum(II) and iridium(III) complexes are also of interest in OLEDs. Preparation of suitable substituted heterocycles led to metal complexes that combine liquid crystallinity and OLED properties; the combination of these properties will be described.

3. Advanced Methods of Organic Synthesis: Plenary lecture PL-6 NOVEL SYNTHESES OF CARBOCYCLES AND HETEROCYCLES VIA IODINE, PALLADIUM AND

ARYNE CHEMISTRY

Iowa State University, Chemistry Department, Ames, USA R.C. Larock larock@iastate.edu

Efficient syntheses of a wide variety of heterocycles and aromatic hydrocarbons have been achieved by the iodocyclization of functionally-substituted alkynes and subsequent palladium-catalyzed cross coupling. Palladium also catalyzes a wide variety of annulation and cyclization reactions useful in carbocycle and heterocycle synthesis. Unique approaches to such substrates are also provided by palladium migration chemistry. Finally, arynes readily undergo a number of annulation reactions, including palladium-catalyzed processes, useful for carbocycle and heterocycle synthesis.

3. Advanced Methods of Organic Synthesis: Plenary lecture PL-7 SOME SERENDIPITIES IN MY RESEARCH LIFE Tsuboi Institute of Science and Technology, Japan

S. Tsuboi stsuboi6@mac.com

Some serendipities found during my research life in Okayama University for 40 years will be presented. Some of them are summarized as shown below.

(1) Vinylogous Favorskii rearrangement was found out for the treatment of chloral acetone and γ-chlorinated α,β-unsaturated ketones with alkaline.¹⁾

(2) A new pyridone synthetic method was discovered by the thermal treatment of imidates of propargyl alcohols and N-cyanopyrrolidine with Professor Larry E. Overman in California University, Irvine.²⁾

(3) Thermal treatment of β-allenic esters with alumina catalyst in aprotic solvents yielded (2E,4Z)-dienoic esters in 57-87% yields with 91-100% stereoselectivity.This method was applied for the synthesis of some natural products such as insect pheromones and leukotrienes, including (E,Z)-diene structure.³⁾

(4) A novel synthesis of tricyclo[5.1.0.0^3,5]octane-2,6-dione derivatives 1 via double Michael addition-induced cyclopropanation reactions was reported. Treatment of 2,4- alkadienoic esters with lithio dichloromethane at -95 ⁰C gave tricyclooctane-2,6-diones 1 as a sole product.⁴⁾

References:

1) Akira Takeda and Sadao Tsuboi, J. Org. Chem., 38, 1709 (1973).

2) L. E. Overman, S. Tsuboi, J. P. Roos, G.F. Taylor, J. Am. Chem. Soc., 102, 747 (1980).

3) A. Takeda, T. Masuda, S. Tsuboi, J. Org. Chem., 47, 4478 (1982).

4) S. Tsuboi, X. Ye, K. Kunito, T. Ono, Tetrahedron, 57, 3035 (2001).

3. Advanced Methods of Organic Synthesis: Plenary lecture PL-8 APPROACHES TO THE SYNTHESIS OF SOME

BIOLOGICALLY ACTIVE COMPOUNDS

The University of Manchester, The School of Chemistry, Manchester, UK

A. Green