Models for the use of .alpha.-amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions

Bueno, M. P.; Cativiela, Carlos; Mayoral, José A.; Avenoza, Alberto

doi:10.1021/jo00023a020

Cited by 42 publications

(29 citation statements)

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“…Substrates 4 and 5 were synthesized as reported. [22] Preparation of Pd·apo-ferritin: Horse spleen ferritin was demineralized with thioglycolic acid to prepare apo-ferritin by a reported procedure. [23] The protein concentration was determined by using the reported extinction coefficient at 280 nm.…”

Section: Methodsmentioning

confidence: 99%

Size‐Selective Olefin Hydrogenation by a Pd Nanocluster Provided in an Apo‐Ferritin Cage

et al. 2004

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Section: Methodsmentioning

confidence: 99%

Size‐Selective Olefin Hydrogenation by a Pd Nanocluster Provided in an Apo‐Ferritin Cage

et al. 2004

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“…[44] After an equimolar amount of acryloyl chloride was dropwise added to an aqueous solution of the sodium salt of L-alanine at 0 8C, the mixture was stirred for 2 h with the temperature increasing to room temperature. It was then acidified to pH ¼ 2-3 with 6 N HCl, and the stirring was continued at room temperature for an additional 1 h. The resulting mixture was extracted three times with ethyl acetate and the solution was dried over anhydrous MgSO 4 .…”

Section: Synthesis Of N-acryloyl-l-alanine (A-ala-oh)mentioning

confidence: 99%

Assembled Structures and Chiroptical Properties of Amphiphilic Block Copolymers Synthesized by RAFT Polymerization of N‐Acryloyl‐L‐alanine

Mori

Matsuyama

Endō

2008

Macro Chemistry & Physics

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Amino acid‐based amphiphilic block copolymers involving poly(N‐acryloyl‐L‐alanine), poly(A‐Ala‐OH), which exhibits a characteristic chiroptical property and pH‐dependent solubility, have been synthesized by reversible addition‐fragmentation chain transfer (RAFT) polymerization. The direct polymerization of A‐Ala‐OH without any protecting chemistry using the dithiocarbamate‐terminated polystyrene or poly(N‐acryloyl‐L‐phenylalanine methyl ester) as a macrochain transfer agent produced well‐defined amphiphilic block copolymers. The self‐assembly behaviors and chiroptical properties of these amphiphilic block copolymers in selective solvents were investigated by dynamic light scattering, circular dichroism, and UV–Vis spectroscopic methods.

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“…The synthesis of vinyl monomer with L ‐alanine (Ac‐ L ‐Ala) was performed by nucleophilic substitution between L ‐alanine and acryloyl chloride according to the previously reported synthetic methods with a slight modification . To a well‐stirred aqueous solution of L ‐alanine (5 g, 5.61 mmol) and sodium hydroxide (4.48 g, 11.22 mmol) in distilled water (20 mL), acryloyl chloride (4.5 mL, 5.61 mmol) was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

Pyrene functionalized side chain alanine and histidine containing copolyacrylates prepared by free radical copolymerization

Murariu¹,

Nechifor²,

Fifere³

et al. 2016

J of Applied Polymer Sci

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An optically active copolyacrylate, poly(N-acryloyl-L-alanine-co-N-acryloyl-L-histidine), is prepared by classical radical copolymerization of N-acryloyl-L-alanine and N-acryloyl-L-histidine, and further chemically modified with 1-pyrene-methanol. The structures of the synthesized compounds are confirmed by spectral analysis (FTIR, 1 H/ 13 C-NMR, UV, fluorescence spectroscopy), thermal methods, and molecular weight measurements. Also, their optical activity is studied using circular dichroism (CD) spectroscopy and optical rotation measurements. The specific rotation values reveal that the direction of rotation of the parent copolymer is dictated by the monomer containing L-alanine. CD data suggest negative and positive Cotton effects regarding the monomers with amino acids. In the case of the unmodified copolymer it is noted the changes of ellipticity values with increasing pH while the random-coil conformation is preserved, which makes it suitable as a pH-responsive system. Photochemical and photophysical investigations reveal that the pyrene-functionalized chiroptical copolyacrylate can be used as a fluorescent chemosensor for the detection of nitro-derivatives in organic media.

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Models for the use of .alpha.-amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions

Cited by 42 publications

References 0 publications

Size‐Selective Olefin Hydrogenation by a Pd Nanocluster Provided in an Apo‐Ferritin Cage

Size‐Selective Olefin Hydrogenation by a Pd Nanocluster Provided in an Apo‐Ferritin Cage

Assembled Structures and Chiroptical Properties of Amphiphilic Block Copolymers Synthesized by RAFT Polymerization of N‐Acryloyl‐L‐alanine

Pyrene functionalized side chain alanine and histidine containing copolyacrylates prepared by free radical copolymerization

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