- Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)
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The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.
- Condon, Sylvie,Le Gall, Erwan,Pichon, Christophe,Presset, Marc,Xavier, Tania
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supporting information
p. 2085 - 2094
(2021/09/02)
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- Asymmetric Syntheses of Chiral Propane-1,3-diols Starting from Malonic Acid
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Syntheses of chiral intermediates having one tertiary asymmetric centre were carried out via chiral half-esters of monoalkylmalonic acids.The menthyl half-ester of ethylmalonic acid afforded a single diastereoisomer through crystallisation-induced asymmetric transformation (second-order asymmertic transformation).Furthermore enantioselective preparation of unsymmertical propane-1,3-diol derivatives was achieved by the use of 8-phenylmenthyl half-esters.
- Ihara, Masataka,Takahashi, Masanobu,Taniguchi, Nobuaki,Yasui, Ken,Fukumoto, Keiichiro,Kametani, Tetsuji
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p. 897 - 903
(2007/10/02)
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- Highly Stereocontrolled Synthesis of the Key Intermediate of 1β-Methylcarbapenem Antibiotic via Intramolecular Nitrone 1,3-Dipolar Cycloaddition
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The key synthetic intermediate of 1β-methylcarbapenem antibiotic, (-)-(3S,4R)-3--4-azetidin-2-one (2), was synthesized from (R)-methyl 3-hydroxy-2-methylpropionate with high stereoselectivity vi
- Ihara, Masataka,Takahashi, Masanobu,Fukumoto, Keiichiro,Kametani, Tetsuji
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