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5.16 Reduction: Enantioselective Hydrovinylation Of Alkenes

T. V. RajanBabu, C. Smith
Published 2012 · Chemistry

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This chapter will provide a brief historical introduction to the hydrovinylation reaction, followed by a discussion of the more recent developments and applications of the asymmetric hydrovinylation reaction. Although the Ni(II)-catalyzed reaction is the major focus of this chapter, other key discoveries involving Fe, Co, Ru, and Pd complexes will also be mentioned. Substrates such as vinylarenes, cyclic and acyclic 1,3-dienes, and strained alkenes undergo efficient heterodimerization with ethylene under catalysis by complexes of these metals. Yields up to 99% can be realized for several of these substrates. Using chiral phospholanes, phosphinites, and finely tuned phosphoramidites as ligands, enantioselectivities greater than 95% enantiomeric excess can be obtained for several substrates. Examples of how ligand tuning, properties of the counter ions, and reaction conditions affect the yields and selectivities of these reactions will be illustrated. One major application of this chemistry is for the installation of an exocyclic stereocenter using a 1-vinylcycloalkene motif. These discoveries provide expeditious routes to several biologically relevant classes of compounds including 2-arylpropionic acids, 1-arylethyl amines, steroid derivatives with uncommon D-ring side chains, helioporins, pseudopterosins and analogs, and pyrrolidinoindolines such as physostigmine and phenserine, which contain all-carbon benzylic quaternary centers.
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