Decarboxylations

Name Reactions

Recent Literature

A base-catalyzed Michael-type addition of sodium diethyl malonate to N-Boc-α-amidoalkyl-p-tolyl sulfones in tetrahydrofuran followed by hydrolysis of the adducts in refluxing 6 M aqueous hydrochloric acid affords β³-amino acid hydrochlorides in high yield and excellent purity.
M. Nejman, A. Śliwińska, A. Zwierzak, Tetrahedron, 2005, 61, 8536-8541.

Diethyl N-Boc-iminomalonate, prepared on multi-gram scale, served as a stable and highly reactive electrophilic glycine equivalent which reacted with organomagnesium compounds affording substituted aryl N-Boc-aminomalonates. Subsequent hydrolysis produced arylglycines.
P. Cali, M. Begtrup, Synthesis, 2002, 63-64.

Related

A novel electrolytic system for non-Kolbe electrolysis based on the acid-base reaction between carboxylic acids and solid-supported bases in MeOH provide the corresponding methoxylated products in excellent yields. The acid-base reaction between carboxylic acids and solid-supported bases preferentially takes place to reduce the cell voltage in MeOH.
T. Tajima, H. Kurihara, T. Fuchigami, J. Am. Chem. Soc., 2007, 129, 6680-6681.

A highly enantioselective, general catalytic system for the facile synthesis of tertiary stereocenters adjacent to cyclic ketones relies on catalytic decarboxylative protonation of readily accessible racemic quaternary β-ketoesters.
J. T. Mohr, T. Nishimata, D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc., 2006, 128, 11348-11349.

Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions of allyl β-keto esters with aldehydes are promoted by Pd(0)- and Yb(III)-DIOP complexes at room temperature. The optimized reaction conditions require the addition of both metals.
S. Lou, J. A. Westbrook, S. E. Schaus, J. Am. Chem. Soc., 2004, 126, 11440-11441.

In the presence of as little as one mol-% of a Lewis acid catalyst, e.g. Mg(ClO₄)₂ or Cu(OTf)₂, carboxylic acids can easily and near quantitatively be protected in a decarboxylative esterification at room temperature as methyl, benzyl, or t-butyl esters.
L. Goossen, A. Döhring, Adv. Synth. Catal., 2005, 345, 943-947.