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Synthesis of β-hydroxy carboxylic acids, esters and amides

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Recent Literature

N-Heterocyclic Carbene-Catalyzed Mukaiyama Aldol Reactions
J. J. Song, Z. Tan, J. T. Reeves, N. K. Yee, C. H. Senanayake, Org. Lett., 2007, 9, 1013-1016.

Simple thioesters undergo direct aldol addition to aldehydes in the presence of a Lewis acid and i-Pr₂NEt. The reactions proceed extremely rapidly and in excellent yield.
J. M. Yost, G. Zhou, D. M. Coltart, Org. Lett., 2006, 8, 1503-1506.

A novel method for Reformatsky-like reactions employs titanocene(III) chloride as a mild and homogeneous single-electron reductant. The reactions are simple, rapid and tolerate a wide range of functionalities. The addition is anti selective.
J. D. Parrish, D. R. Shelton, R. D. Little, Org. Lett., 2003, 5, 3615-3617.

An easy, direct, general, and efficient samarium diiodide-mediated preparation of 3-hydroxyacids in high yield by reaction of different aldehydes or ketones with commercially available iodoacetic acid is described.
J. M. Concellón, C. Concellón, J. Org. Chem., 2006, 71, 4428-4432.

Efficient In- or In(I)-based diastereoselective Reformatsky-type reactions of simple ketones, α-alkoxy ketones, and β-keto esters were developed. High anti selectivity was established in the addition of the branched α-halo ester derivatives to simple ketones using indium metal under THF-refluxing conditions. Syn selective additions to α-alkoxy ketones and β-keto esters required either In(I)X or In-InCl₃ systems in toluene under ultrasonication.
S. A. Babu, M. Yasusa, I. Shibata, A. Baba, J. Org. Chem., 2005, 70, 10408-10419.

S. A. Babu, M. Yasusa, I. Shibata, A. Baba, J. Org. Chem., 2005, 70, 10408-10419.

The addition of amide enolates to acylsilanes and a subsequent 1,2-Brook rearrangement generate β-silyloxy homoenolates nucleophiles that undergo smooth addition to alkyl halides, aldehydes, and ketones.
R. B. Lettan II, T. E. Reynolds, C. V. Galliford, K. A. Scheidt, J. Am. Chem. Soc., 2006, 128, 15566-15567.

A tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl glycolate esters generates two carbon-carbon bonds and two contiguous stereocenters with excellent diastereoselectivity in a single step from simple starting materials. The [1,2]-Wittig rearrangement proceeds under very mild reaction conditions.
M. B. Betrand, J. P. Wolfe, Org. Lett., 2006, 8, 4661-4663.

Chiral rhodium(bisoxazolinylphenyl) complexes efficiently catalyze the asymmetric reductive aldol reaction of aldehydes and α,β-unsaturated esters with hydrosilanes to give the corresponding β-hydroxypropionates with high anti-selectivity and enantioselectivity. The selectivity is discussed.
H. Nishiyama, T. Shiomi, Y. Tsuchiya, I. Matsuda, J. Am. Chem. Soc., 2005, 127, 6972-6973.

A new strategy for the catalytic asymmetric aldol reaction of ketones was developed that relies on a chiral copper(I) complex-catalyzed domino reduction/aldol reaction sequence in the presence of phenylsilane.
J. Deschamp, O. Chuzel, J. Hannedouche, O. Riant, Angew. Chem. Int. Ed., 2006, 45, 1292-1297.

The weakly acidic species, silicon tetrachloride (SiCl₄), can be activated by binding of a strongly Lewis basic chiral phosphoramide, leading to in situ formation of a chiral Lewis acid for catalysis of the aldol reaction of conjugated and nonconjugated aldehydes with silyl ketene acetals and silyl dienol ethers (vinylogous aldol reactions). The high levels of regio-, anti diastereo-, and enantioselectivity observed are discussed.
S. E. Denmark, G. L. Beutner, T. Wynn, M. D. Eastgate, J. Am. Chem. Soc., 2005, 127, 3774-3789.

C-H functionalization of benzyl silyl ethers by means of rhodium-catalyzed insertions of aryldiazoacetates can be achieved in a highly diastereoselective and enantioselective manner by judicious choice of chiral catalyst or auxiliary. The use of (S)-lactate as a chiral auxiliary resulted in C-H functionalization with moderate diastereoselectivity and enantioselectivity. The best results were achieved using Hashimoto's Rh₂((S)-PTTL)₄ catalyst.
H. M. L. Davies, S. J. Hedley, B. R. Bohall, J. Org. Chem., 2005,70, 10737-10742.

Related

The catalytic generation of activated carboxylates from epoxyaldehydes enables a direct, anti-selective, convenient and mild synthesis of β-hydroxyesters.
K. Y.-K. Chow, J. W. Bode, J. Am. Chem. Soc., 2004, 126, 8126-8127.

A mild, enantioselective hydrosilylation of 3-oxo-3-arylpropionic acid methyl or ethyl esters using axially chiral BINAM N-heterocyclic carbene (NHC)-Rh(III) complexes as catalysts gave 3-hydroxy-3-arylpropionic acid methyl or ethyl esters in good yields with good to excellent enantioselectivities under mild conditions.
. Xu, X. Gu, S. Liu, Q. Duo, M. Shi, J. Org. Chem., 2007, 72, 2240-2242.