Spontaneous and induced generation of optical activity in racemic 1,1′-Binaphthyl

Pincock, Richard E.; Bradshaw, Richard P.; Perkins, Robert

doi:10.1007/bf01732772

Cited by 13 publications

(3 citation statements)

References 7 publications

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“…38 In dynamic crystallization, it has been reported that, of the many additives tested during optical resolution by crystallization of binaphthyl, only mandelic acid and tartaric acid could perform chirality control. 39 In addition, in the dynamic crystallization of the imine of the amino acid derivative phenylglycine amide, it has been reported that the addition of optically active phenylglycine gives priority to the reverse stereochemical crystals. 40 Only a limited number of optically active additives can control the chirality of crystal growth in any of the preferred crystallizations.…”

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“…For example, in the preferential crystallization of asparagine and glutamine without dynamic racemization, there is a pioneering report in which the reversal effect controls mirror images in which several amino acids are preferentially obtained . In dynamic crystallization, it has been reported that, of the many additives tested during optical resolution by crystallization of binaphthyl, only mandelic acid and tartaric acid could perform chirality control . In addition, in the dynamic crystallization of the imine of the amino acid derivative phenylglycine amide, it has been reported that the addition of optically active phenylglycine gives priority to the reverse stereochemical crystals .…”

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confidence: 99%

“…In addition, in the dynamic crystallization of the imine of the amino acid derivative phenylglycine amide, it has been reported that the addition of optically active phenylglycine gives priority to the reverse stereochemical crystals . Only a limited number of optically active additives can control the chirality of crystal growth in any of the preferred crystallizations. − This is because highly substrate-selective interactions are indispensable between the chiral crystals of the substrate and the chiral additives.…”

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confidence: 99%

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Behavior of All Chiral Standard Amino Acids for Chiral Symmetry Breaking of p-Anisoin

Miyazaki

Sanada

Nakamura

et al. 2022

Crystal Growth & Design

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The asymmetric amplification of p-anisoin was studied by attrition-enhanced deracemization in the presence of chiral standard amino acids. In this reaction, p-anisoin crystallized as a conglomerate, and deracemization under basic conditions was efficiently performed in 99% ee by Viedma ripening. Although the handedness of the enantioselective crystallization cannot be controlled by spontaneous crystallization, it could be governed by the coexistence of a catalytic amount of 16 chiral amino acids except cysteine, serine, and threonine. l-Amino acids tilted the handedness of enantiomer crystals to (R)-anisoin, while d-amino acids tilted it toward (S)-isomer crystals. It was clarified that this is due to the asymmetric transformation of p-anisoin in the mother liquor by the enantiomeric amino acids. The same slight asymmetric transformation in the solution phase was observed in α-hydroxyketones such as acetoin. Though the Soai reaction for an autocatalytic and asymmetric amplification system in the presence of a variety of chiral sources is famous, the crystallization-induced dynamic deracemization of p-anisoin provides the first chirality control system to be tilted by the enantioselective crystallization derived from many chiral additives.

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confidence: 99%

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Behavior of All Chiral Standard Amino Acids for Chiral Symmetry Breaking of p-Anisoin

Miyazaki

Sanada

Nakamura

et al. 2022

Crystal Growth & Design

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Origins of Chiral Homogeneity in Nature

Bonner¹

1988

Topics in Stereochemistry

120

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Synthesis, Structure, and Solvent‐Induced Spontaneous Homochiral Assembly of Bidentate Bis(N,N′‐diaryl‐N‐heterocyclic carbene)‐Palladium Complexes

et al. 2008

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A series of new bidentate bis(N‐heterocyclic carbene)‐palladium complexes 4a–e and 6 with xanthene framework was synthesized. The X‐ray analyses of the complexes revealed that the complexes have conformational chirality. Homochiral crystals of 4a and 6 were obtained by recrystallization from THF or 1,4‐dioxane as solvent. The energy barriers for racemization of the complexes were calculated from dynamic NMR spectroscopy. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Spontaneous and induced generation of optical activity in racemic 1,1′-Binaphthyl

Cited by 13 publications

References 7 publications

Behavior of All Chiral Standard Amino Acids for Chiral Symmetry Breaking of p-Anisoin

Behavior of All Chiral Standard Amino Acids for Chiral Symmetry Breaking of p-Anisoin

Origins of Chiral Homogeneity in Nature

Synthesis, Structure, and Solvent‐Induced Spontaneous Homochiral Assembly of Bidentate Bis(N,N′‐diaryl‐N‐heterocyclic carbene)‐Palladium Complexes

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