Asymmetric phase transfer catalysed Michael additions and their application in synthesis

This thesis describes an investigation into organocatalysed asymmetric Michael additions and their application in synthesis. It focuses primarily on phase transfer catalysed processes, however other modes of catalysis are briefly investigated. Firstly, β-ketoesters derived from 1-indanone and l-tetr...

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Main Author:	Beynon, Christopher
Published:	University of Nottingham 2012
Subjects:	541.39
Online Access:	http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.588066

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spelling	ndltd-bl.uk-oai-ethos.bl.uk-5880662015-03-20T04:57:29ZAsymmetric phase transfer catalysed Michael additions and their application in synthesisBeynon, Christopher2012This thesis describes an investigation into organocatalysed asymmetric Michael additions and their application in synthesis. It focuses primarily on phase transfer catalysed processes, however other modes of catalysis are briefly investigated. Firstly, β-ketoesters derived from 1-indanone and l-tetralone are examined as potential Michael donors. Their addition to methyl vinyl ketone is studied, with a view to producing members of the Gibberellin family. Secondly, the use of an achiral phenoxide "co-catalyst" in conjunction with a chiral quaternary ammonium salt, derived from cinchonidine, is found to produce an effective catalytic species. It is shown to promote the addition of benzophenone glycine imines to a range of Michael acceptors in excellent levels of enantiocontrol (>90% ee). The Michael adducts are then successfully converted to their corresponding 2,5-disubstituted pyrrolidine species, with high maintenance of stereocontrol. A potential application of this co-catalyst methodology is then described in studies towards the synthesis of kaitocephalin.541.39University of Nottinghamhttp://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.588066Electronic Thesis or Dissertation
collection	NDLTD
sources	NDLTD
topic	541.39
spellingShingle	541.39 Beynon, Christopher Asymmetric phase transfer catalysed Michael additions and their application in synthesis
description	This thesis describes an investigation into organocatalysed asymmetric Michael additions and their application in synthesis. It focuses primarily on phase transfer catalysed processes, however other modes of catalysis are briefly investigated. Firstly, β-ketoesters derived from 1-indanone and l-tetralone are examined as potential Michael donors. Their addition to methyl vinyl ketone is studied, with a view to producing members of the Gibberellin family. Secondly, the use of an achiral phenoxide "co-catalyst" in conjunction with a chiral quaternary ammonium salt, derived from cinchonidine, is found to produce an effective catalytic species. It is shown to promote the addition of benzophenone glycine imines to a range of Michael acceptors in excellent levels of enantiocontrol (>90% ee). The Michael adducts are then successfully converted to their corresponding 2,5-disubstituted pyrrolidine species, with high maintenance of stereocontrol. A potential application of this co-catalyst methodology is then described in studies towards the synthesis of kaitocephalin.
author	Beynon, Christopher
author_facet	Beynon, Christopher
author_sort	Beynon, Christopher
title	Asymmetric phase transfer catalysed Michael additions and their application in synthesis
title_short	Asymmetric phase transfer catalysed Michael additions and their application in synthesis
title_full	Asymmetric phase transfer catalysed Michael additions and their application in synthesis
title_fullStr	Asymmetric phase transfer catalysed Michael additions and their application in synthesis
title_full_unstemmed	Asymmetric phase transfer catalysed Michael additions and their application in synthesis
title_sort	asymmetric phase transfer catalysed michael additions and their application in synthesis
publisher	University of Nottingham
publishDate	2012
url	http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.588066
work_keys_str_mv	AT beynonchristopher asymmetricphasetransfercatalysedmichaeladditionsandtheirapplicationinsynthesis
_version_	1716788102150750208

Asymmetric phase transfer catalysed Michael additions and their application in synthesis

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