Categories: C=O Bond Formation > Synthesis of carboxylic acids >
Synthesis of carboxylic acids by hydrolysis or deprotection
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(R)-β-Hydroxy nitriles were obtained via a reduction catalyzed by a
recombinant carbonyl reductase with excellent optical purity and were further
converted to (R)-β-hydroxy carboxylic acids via a nitrilase-catalyzed
hydrolysis. The present study allows ready access to both chiral β-hydroxy
nitriles and β-hydroxy carboxylic acids of pharmaceutical importance.
D. Zhu, H. Ankati, C. Mukherjee, Y. Yang, E. R. Biehl, L. Hua, Org. Lett., 2007,
9, 2561-2563.
Simple, mild, and environmentally friendly procedures for the direct conversion
of dithioesters into either carboxylic acids or esters using hydrogen peroxide
under alkaline conditions are described.
F. Grellepois, C. Portella, Synthesis, 2008,
3443-3446.
The reaction of aldehydes with trichloromethide followed by reductive ring
opening under basic conditions
affords homologated carboxylic acids in high yields. This operationally simple
procedure provides a practical, efficient alternative to other homologation
protocols and is compatible with sensitive aldehydes including enals
and enolizable substrates.
L. R. Cafiero, T. S. Snowden, Org. Lett.,
2008,
10, 3853-3856.
L. R. Cafiero, T. S. Snowden, Org. Lett.,
2008,
10, 3853-3856.
The reaction of alkenyl trichloromethyl carbinols with various nucleophiles
under protic basic conditions reveals that mercaptans participate by
α-substitution (SN2), wheareas hydroxide prefers γ-substitution
with stereoselective allylic transposition (SN2').
Regioselectivity with alkoxides depends upon alkene substitution.
J. L. Shamshina, T. S. Snowden, Org. Lett., 2006, 8, 5881-5884.
