Sml2-mediated Reactions - the Basics

The additives commonly utilized to alter the reducing power of Sml2 are classified into two major types (a) basic cosolvents such as HMPA and DMPU, (b) inorganic salts such as LiX, NiX2, and FeXs. This section will provide a brief introduction to the application of various additives utilized in Sml2 mediated reactions. 

In one of the few examples of a chiral ligand-controlled asymmetric reaction mediated by Sml2, Mikami reported the use of the chiral, bis-phosphine oxide, BINAPO (4), as a Lewis basic additive.23 For example, reductive coupling of methyl acrylate and acetophenone using Sml2 in THF with 2 equiv of BINAPO gave lactone 5 in 46% yield and 67% ee (Scheme 2.8).23... 

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