New Convenient Access to Optically Active Methylidenecyclopropylcarbinols

Corre, M. Le; Hercouet, A.; Bessieres, Bernard

doi:10.1021/jo00097a066

Cited by 27 publications

(31 citation statements)

References 0 publications

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“…11 Oxidation of alcohol 3 under standard Swern reaction conditions furnished a-methylenecyclopropanal 4. 12 This rather unstable compound was used in subsequent steps (Scheme 1).…”

Section: Figurementioning

confidence: 99%

Synthesis of (±)-(2-Methylenecyclopropyl)glycine and (±)-4-[(Amino(carboxymethyl)]spiro[2.2]pentane-1-carboxylic Acid

Averina¹,

Yashin²,

Grishin³

et al. 2006

Synthesis

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“…11 Oxidation of alcohol 3 under standard Swern reaction conditions furnished a-methylenecyclopropanal 4. 12 This rather unstable compound was used in subsequent steps (Scheme 1).…”

Section: Figurementioning

confidence: 99%

Synthesis of (±)-(2-Methylenecyclopropyl)glycine and (±)-4-[(Amino(carboxymethyl)]spiro[2.2]pentane-1-carboxylic Acid

Averina¹,

Yashin²,

Grishin³

et al. 2006

Synthesis

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“…A second crop (1.29 g) was obtained after concentration of the mother liquor and recrystallization of the residue from the same solvent (ca. 25 [9] Anhydrous DMF (0.1 mL) and oxalyl chloride (15.2 g, 10.3 mL, 120 mmol) were added at ambient temperature to a stirred solution of the respective carboxylic acid (100 mmol) in anhydrous CH 2 Cl 2 (50 mL), and the mixture was stirred until the gas evolution had ceased (1Ϫ2 h). Then the solvent was evaporated under reduced pressure (15Ϫ20 Torr) without heating until the temperature of the reaction flask had reached ca.…”

Section: Exo-6-(methoxycarbonyl)bicyclo[310]hexane-6-carboxylicmentioning

confidence: 99%

Synthesis and Radical Polymerization of Various 2‐Cyclopropylacrylates

Meijere¹,

Bagutski²,

Zeuner³

et al. 2004

Eur J Org Chem

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Fourteen new alkyl 2-cyclopropylacrylates 1a−n with various substituents R 1 −R 5 were synthesized from readily available precursors by applying standard transformations such as cyanohydrin formation from an aldehyde, alcoholysis to an α-hydroxycarboxylic ester, oxidation and Wittig methylenation of an α-oxocarboxylic ester. Overall yields ranged from 33 to 54%. A new method for the hydrolysis of dimethyl cyclopropanedicarboxylates to the corresponding half-esters was developed. The α-oxocarboxylates 7g−n were prepared by dirhodium tetraacetate catalyzed cyclopropanation of alkenes 8g−n with methyl or ethyl diazopyruvate in 32−58% yield. The monomers 1a−n were characterized by 1 H, 13 C NMR spectroscopy, mass spectrometry and elemental analysis. The radical homopolymerizations of 1a−n were carried out with 2,2Ј-azabisisobutyronitrile (AIBN) as initiator in chloroben-

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“…The title compound (Bagutski, 2003), (I), was prepared by methanolysis of the cyanohydrine, (III), obtained from the known methylenecyclopropanecarboxaldehyde, (II) (Le Corre et al, 1994), as a key intermediate along the route to new vinylcyclopropane monomers for radical ring-opening polymerization (Moszner et al, 2003;de Meijere et al, 2004). The crude mixture of diastereomers was separated by column chromatography and one of the two diastereomers gave good quality crystals.…”

Section: Commentmentioning

confidence: 99%