Abstract
This short review describes the methods of single carbon insertion reactions into carbonyl compounds.
Highlights
Single carbon insertion via β-oxido carbenoid intermediatesThe Yamamoto method is presented in more detail in Scheme 2
The homologation of carbonyl compounds by single carbon insertion reactions Alan R
Most insertions into cyclic ketones and aromatic or aliphatic aldehydes are regioselective with formation of single regioisomers; insertions into aryl-alkyl ketones lead to both aryl- and alkyl-migration
Summary
The Yamamoto method is presented in more detail in Scheme 2. The modification by Satoh and Yamakawa3a–c of this method for the one-carbon homologation of carbonyl compounds is based on the rearrangement of β-oxido carbenoids 4 generated via ligand exchange of the sulfinyl group of α-chloro β-hydroxy sulfoxide 3 with tBuLi to give homologated ketones 5 (Scheme 3): Table 1 shows examples where selective migration occurs to form a single regioisomer. Satoh and Miyashita reported one-carbon homologations of cyclic ketones by treatment of adducts 2 derived from the 1-chloroalkyl sulfoxides 1 with t-BuMgCl or LDA followed by reaction with i-PrMgCl. the enolate intermediates 7 generated in situ from the rearrangement of 6 were trapped with an electrophile to give the α,α-disubstituted homologated ketones 8 (Scheme 4) (Table 2).3a
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