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Chiral Amine Synthesis: Methods, Developments and by Thomas C. Nugent PDF

By Thomas C. Nugent

ISBN-10: 3527325093

ISBN-13: 9783527325092

ISBN-10: 3527629556

ISBN-13: 9783527629558

This primary finished presentation of this sizzling and significant subject compiles the main updated equipment for chiral amine synthesis. The overseas record of authors reads like a "Who's Who" of the topic, offering a wide array of hugely useful info centred into the beneficial and crucial methods.Following an introductory bankruptcy dedicated to aiding readers fast verify which options to decide on for his or her research, this guide and prepared reference specializes in the exam of equipment which are trustworthy and concurrently effective for the synthesis of structurally varied aliphatic and fragrant chiral amines. sleek tools and purposes present in (pharmaceutical) also are coated.

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2, in which the Lewis acidic magnesium atom is believed to activate the imine. In addition, cleavage of the chiral auxiliary occurs under mild acidic conditions to generate a-branched amines 36 [57]. 2, entries 17–20) [59, 60]. 16), a reaction that has been primarily developed for catalytic asymmetric processes (see below). The hydrogenation of 1,3-enynes or 1,3-diynes in the presence of N-sulfinyliminoesters enables highly regio- and stereoselective reductive coupling to afford diene- and enyne-containing a-amino acid esters [62].

2 Imines Bearing a Chiral Protecting/Activating Group One of the most practical methodologies used to generate a-branched amines relies on the stoichiometric use of covalently bonded chiral auxiliaries on the nitrogen substituent. 4). The imine 19 derived from a-phenylethylamine has been reported to react with various nucleophiles, such as organolithium reagents and cuprates, to generate the diastereoenriched amine following hydrogenolysis (H2/Pd) of the chiral auxiliary. However, the diastereoselectivities of these reactions are typically modest [36–38].

3 Diastereoselective addition to N-sulfinyl ketimines. O N R1 S O t-Bu 1. Me3Al, Toluene t-Bu 2. 4 Catalytic Asymmetric Nucleophilic Addition to Achiral Imines j15 feature of this methodology is the ability to generate the starting imine as a major diastereomer. 3, entries 12 and 13) [66]. 17) [67]. This report was quickly followed by Soai [68], who showed that a chiral amino alcohol can also be used in the nucleophilic addition of diorganozinc to N-diphenylphosphinoyl imines. Four years after Tomioka’s seminal report, Denmark disclosed that sparteine [69] and bisoxazolines [70] can be used in catalytic amounts in the transfer of organolithium reagents to N-aryl imines.

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Chiral Amine Synthesis: Methods, Developments and Applications by Thomas C. Nugent


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