Nucleophilic Substitutions at Aliphatic Carbon

An important issue is the right choice of substrate 1 which functions as an anion precursor. Successful organocatalytic conversions have been reported with indanones and benzophenone imines of glycine derivatives. The latter compounds are, in particular, useful for the synthesis of optically active a-amino acids. Excellent enantioselectivity has been reported for these conversions. In the following text the main achievements in this field of asymmetric organocatalytic nucleophilic substitutions are summarized [1, 2], The related addition of the anions 2 to Michael-acceptors is covered by chapter 4. 

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Crossing the Borderline Between Sn1 and Sn2 Nucleophilic Substitution at Aliphatic Carbon... 

Nucleophilic substitution at aliphatic carbon is a reaction that plays an important role in organic synthesis. The use of the reaction in construction of carbon-carbon bonds will be discussed in Part B, but the role of the reaction in interconverting certain functional groups has such a basic place in organic chemistry that it is appropriate to illustrate some examples of the synthetic utility of nucleophilic substitution. The conversion of alcohols to alkyl halides and the conversion of alcohols to ethers are among the most fundamental organic transformations. 

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