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- W2009968328 abstract "This thesis describes the development of new methods for the asymmetric synthesis of α-alkoxy and α-amino organometallic reagents. Two approaches were taken: (i)sulfoxide → magnesium exchange; (ii) asymmetric lithiation-trapping using chiral bases. A review of this area is provided in Chapter One.Chapter Two details the synthesis of α-alkoxy sulfoxides A in 99:1 er by asymmetric lithiation using s-BuLi and chiral diamines and trapping with Andersen’s sulfinate. Inaddition, an investigation into the lack of stereospecificity at sulfur during the trappingprocess is presented. Finally, a sulfoxide → magnesium exchange was used to convert the α-alkoxy sulfoxides into α-alkoxy Grignard reagents B and subsequent trappingallows access to a range of products as single enantiomers. The remarkable configurational stability of α-alkoxy Grignard reagents when compared to their organolithium counterparts is of particular note.Attempts to use a similar method to synthesise α-amino sulfoxides in 99:1 er is described in Chapter Three. Furthermore, insights are given into the surprisinginstability of unsubstituted α-amino sulfoxides. Novel α-amino sulfoxides C were designed to prohibit sulfoxide elimination. From the isolatable α-amino sulfoxides, thesynthesis and reactions of α-amino Grignard reagents D in 99:1 er via sulfoxide → magnesium exchange is reported.In Chapter Four, an investigation into the mechanism of the asymmetric lithiation trapping of N-thiopivaloyl azetidine E using s-BuLi and chiral diamines is presented. The configurational stability of the organolithium intermediate F was determined at −78°C and the scope of electrophilic trapping was investigated." @default.
- W2009968328 created "2016-06-24" @default.
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- W2009968328 date "2013-07-01" @default.
- W2009968328 modified "2023-09-23" @default.
- W2009968328 title "The asymmetric synthesis and reactions ofα-functionalised organometallic reagents" @default.
- W2009968328 hasPublicationYear "2013" @default.
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