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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Synthesis, Structure and Application of α, β Dehydro-α-aminophosphonic and α,β-Dehydro-α-aminophosphinic Acid Derivatives

Author(s): Anna Kuznik, Roman Mazurkiewicz and Nikodem Kuznik

Volume 10, Issue 3, 2013

Page: [411 - 424] Pages: 14

DOI: 10.2174/1570179411310030006

Price: $65

Abstract

The synthesis of α,β-dehydro-α-aminophosphonic and α,β-dehydro-α-aminophosphinic acid derivatives is discussed. The most important synthetic pathways to the above-mentioned compounds have been divided into four groups depending on the type of bond formed as the last one. The configuration at the C=C double bond can be established based on the specific coupling constants 3JHP and 3JCP for the appropriate Z- and E-stereoisomers. The application of α,β-dehydro-α-aminophosphonates and α,β-dehydro-α- aminophosphinates, particularly in the enantioselective catalytic hydrogenation, is also discussed.

Keywords: α -aminophosphinic acids, α -aminophosphonic acids, asymmetric catalytic hydrogenation, α , β -dehydro-α-aminophosphinates, , β-dehydro-α-aminophosphonates, Michaelis-Arbuzov reaction, Wadsworth-Emmons reaction.


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