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EP/K005391/1 - Cascade Catalysis: From Alkynes to Polycycles

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Dr EA Anderson EP/K005391/1 - Cascade Catalysis: From Alkynes to Polycycles

Principal Investigator - Oxford Chemistry, University of Oxford

Scheme

Standard Research

Research Areas

Catalysis Catalysis

Synthetic Organic Chemistry Synthetic Organic Chemistry

Start Date

01/2013

End Date

01/2015

Value

£235,426

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Grant Description

Summary and Description of the grant

The efficient and rapid preparation of cyclic (ring-containing) organic molecules is one of the most important challenges for organic chemists. The construction of these molecules as single enantiomers - that is, one of two mirror image forms which are related as are left and right hands - is an equally vital consideration for modern applications of organic chemistry. In this proposal, we aim to develop chemistry which prepares multiple ring systems by short synthetic routes, and as single enantiomers (i.e asymmetrically).

We will achieve this aim through the use of palladium catalysts to control the formation of ring systems which are connected to alkynes (carbon-carbon triple bonds). In this arena, our group has established itself as an internationally leading team through a recent high profile publication, and in this project we intend to expand our understanding and use of this reaction principle to prepare complex but fundamentally useful ring systems containing oxygen and nitrogen atoms - heterocycles - which form the core of many pharmaceuticals and agrochemicals.

In our planned chemistry, the alkyne serves not only to mediate ring formation through its interaction with the palladium catalyst, but is also a valuable functional group in its own right which can undergo a wide range of useful chemistry after the ring-forming step. We intend to use the unique properties of the alkyne to explore the formation of additional ring systems.

While we expect these processes to be successful, of greater ambition and adventure is the preparation of multiple rings in a single step using "cascade" reactions, processes which intrinsically lead to higher reaction efficiency and yields than the previously described separate reaction sequences - a principle which fundamentally links to the EPSRC Dial-A-Molecule Grand Challenge. The reactions we propose to study in this context also form their respective products as single stereoisomers (i.e. single three-dimensional structures where several possibilities exist). This is important, as applications in the design of new pharmaceuticals will rely on this selectivity.

The project also aims to push boundaries in sequenced and dual catalysis - where multiple catalytic reactions take place in direct succession, either in separate reactions (sequenced) or more ambitiously and appealingly in the same reaction flask (dual catalysis). This leads to even greater molecular complexity but with no extra cost to the number of steps needed to prepare starting materials, and is an area at the forefront of catalysis research.

In summary, we aim to employ new and contemporary catalytic processes to build molecules in a flexible and novel fashion. The variety of functional groups we intend to explore in these processes will lead to a broad expanse of product types, which will enhance possibilities for applications in medicinal chemistry, agrochemicals, chemical biology, and materials chemistry.

Structured Data / Microdata


Grant Event Details:
Name: Cascade Catalysis: From Alkynes to Polycycles - EP/K005391/1
Start Date: 2013-01-31T00:00:00+00:00
End Date: 2015-01-30T00:00:00+00:00

Organization: University of Oxford

Description: The efficient and rapid preparation of cyclic (ring-containing) organic molecules is one of the most important challenges for organic chemists. The construction of these molecules as single enantiomers - that is, one of two mirror image forms which are rel ...