Производные α-аминокислот, содержащие фрагмент ионной жидкости - регенерируемые органокатализаторы асимметрической альдольной реакции в водной среде тема диссертации и автореферата по ВАК РФ 02.00.03, кандидат химических наук Сиюткин, Дмитрий Евгеньевич

• Сиюткин, Дмитрий Евгеньевич
• кандидат химических наук
• 2009

Оглавление диссертации кандидат химических наук Сиюткин, Дмитрий Евгеньевич

Список сокращений

I. Введение

II. Альдольные реакции в присутствии воды (литуратурный обзор)

11.1. Альдольные реакции в водных растворах

11.2. Альдольные реакции в водных органических растворителях

11.3. Альдольные реакции в 2-х фазных системах: реагенты - вода 25 П.3.1. Асимметрические альдольные реакции в водной среде в присутствии растворимых в воде органокатализаторов

11.3.2. Асимметрические альдольные реакции в водной среде в присутствии гидрофобных органокатализаторов, содержащих пирролидиновый цикл

11.3.3. Асимметрические альдольные реакции в водной среде в присутствии гидрофобных органокатализаторов, пе содержащих пирролидиновый цикл

Заключение диссертации по теме «Органическая химия», Сиюткин, Дмитрий Евгеньевич

V. Выводы

1. Предложены подходы к созданию нового типа регенерируемых органокатализаторов асимметрической альдольной реакции в водной среде, содержащих в своем составе фрагменты ионных жидкостей (ИЖ). На их основе синтезированы производные (411)-4-гидрокси-(8)-пролина, (8)-серина, (8)-треонина со свободными карбоксильными группами, а таюке амиды (4К.)-4-гидрокси-(8)-пролина с а,а-дифенил-(8)-валинолом, содержащие алкилзамещепные катионы имидазолия или пиридиния и различные, в том числе фторсодержащие, анионы.

2. Установлено, что синтезированные а-амипокислоты, содержащие анионы Ply, и NTf2" наряду с длшшоцепными алкильными заместителями, а также амиды пролина, модифицированные фрагментами ИЖ, эффективно катализируют асимметрические альдольиые реакции в водной среде, что позволило осуществить на их основе диастерео- и энантиоселективный синтез широкого круга хиральных Р-гидроксикарбонильных соединений различного строения.

3. Обнаружено, что разработанные катализаторы легко регенерируются и могут быть использованы в изученных реакциях многократно (до 8 раз) без уменьшения их диастерео- и энантиоселективности.

4. На основании полученных экспериментальных данных высказано предположение о том, что в предложенных условиях реакции под действием катализаторов, содержащих фрагменты ИЖ, протекают преимущественно на границе раздела водной и органической фаз (фазы реагентов), где, благодаря своей амфифильной структуре, располагается модифицированный ИЖ катализатор.

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