Categories: C-C Bond Formation > Oxygen-containing molecules >
Homologations and chain extensions
Name Reactions
Recent Literature
The reaction of β-keto esters with CF3CO2ZnCH2I
provided the corresponding chain-extended products in moderate to good
yields. α-Substituted acyclic β-keto esters reacted less efficiently than
cyclic β-keto esters or simple β-keto esters.
S. Xue, Y.-K. Liu, L.-Z. Li, Q.-X. Guo, J. Org. Chem., 2005,
70, 8245-8247.
A mild, green, and convenient one-pot carbon-chain extension of carboxylic acids
with the assistance of microwaves and lithium chloride avoids the use of
corrosive reagents, is tremendously faster than previously methods, and was free
of configurational isomerization. Notably, LiCl played a dual role in the
Krapcho decarboxylation and subsequent ester hydrolysis under neutral conditions.
C. Wang, J. Su, Y. Li, S. Gao, X. Huo, B. Yi, G. Zhao, Synlett, 2023,
34,
1033-1036.
S. Xue, Y.-K. Liu, L.-Z. Li, Q.-X. Guo, J. Org. Chem., 2005,
70, 8245-8247.
The conversion of β-keto esters into β-methylated and phenylated γ-keto esters
can be achieved through treatment with zinc carbenoids derived from
1,1-diiodoethane and diiodotoluene, respectively.
W. Lin, R. J. McGinness, E. C. Wilson, C. K. Zercher, Synthesis, 2007,
2404-2408.