Asymmetric transformation by dynamic crystallization of achiral succinimides

Hachiya, Shoko; Kasashima, Yoshio; Yagishita, Fumitoshi; Mino, Takashi; Masu, Hyuma; Sakamoto, Masami

doi:10.1039/c3cc41678j

Cited by 28 publications

(24 citation statements)

References 31 publications

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“…So far, experiments by Hachiya et al. approximate this goal most closely, but using total spontaneous resolution instead . They succeeded in partially converting molecules with two identical stereocenters (meaning their system consisted of only three stereoisomers (one pair of enantiomers ( 1 ) and the corresponding achiral meso compound) instead of four stereoisomers (two pairs of enantiomers), Figure ).…”

Section: Figurecontrasting

confidence: 59%

Solid‐Phase Conversion of Four Stereoisomers into a Single Enantiomer

Engwerda¹,

Mertens²,

Tinnemans³

et al. 2018

Angew Chem Int Ed

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Viedma ripening is an emerging method for the solid‐phase deracemization of mixtures of enantiomers. Up to now, the scope of the method has remained limited to molecules with a single stereocenter. We show here that this method can be extended to obtain a single enantiomer from a mixture of stereoisomers with two different stereocenters. In addition, we show that by using tailor‐made chiral additives, the conversion time can be reduced by a factor of 100.

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Section: Figurecontrasting

confidence: 59%

Solid‐Phase Conversion of Four Stereoisomers into a Single Enantiomer

Engwerda¹,

Mertens²,

Tinnemans³

et al. 2018

Angew Chem Int Ed

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“…[3][4][5][6][7] Since its discovery in 2005, severalc onditions and parameters weres creened to improve the efficiency of this technique. [1,[8][9][10] Organic compounds, such as amino acids and their derivatives, [11,12] organometallic complexes [13] and pharmaceutical intermediates, [4,5] were successfully deracemized by using Viedma ripening. Duringt he process, as lurry of the conglomerate crystalsi nas aturated solution is intensively ground to promote breakage and dissolution as well as growth of the crystals.…”

Section: Introductionmentioning

confidence: 99%

Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Belletti

Tortora

Mellema³

et al. 2019

Chemistry A European J

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Viedma ripening is ad eracemizationp rocess that has been used to deracemize ar ange of chiral molecules. The method hast wo major requirements:t he compound needs to crystallize as ac onglomerate and it needs to be racemizable under the crystallization conditions. Although conglomerate formation can be induced in different ways, the number of racemization methods is still ratherl imited. To extend the scope of Viedma ripening, in the present research we applied UV-light-induced racemization in a Viedmar ipening process, and report the successful deracemizationo faB INOL derivative crystallizing as ac onglomerate. Irradiation by UV light activatest he target compound in combination with an organic base, required to promote the excited-state proton transfer (ESPT), leadingt hereaftert o racemization. This offers an ew tool towards the development of Viedma ripening processes, by using ac heap and "green"c atalytic source like UV light to racemize suitable chiral compounds.

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“…Asymmetric synthesis from prochiral starting materials by using only crystal chirality under absolutely achiral conditions, that is, absolute asymmetric synthesis, has been investigated by many methods, including solid‐state photochemical reactions and asymmetric reactions by using frozen chirality . Recently, elegant examples of asymmetric synthesis have been demonstrated by combining chemical reactions providing asymmetric centers with dynamic selective crystallization, and products with high ee values without an external chiral source have been obtained . In such cases, the dynamic crystallization process involves an enolate anion under basic conditions, and a reversible reaction by thermal racemization .…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis Involving Reversible Photodimerization of a Prochiral Flavonoid Followed by Crystallization

et al. 2017

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Asymmetric synthesis involving photochemical dimerization of a prochiral flavonoid derivative in solution without any chiral source was achieved. Irradiation of ethyl 6‐bromochromonecarboxylate in solution efficiently gave a C2‐chiral anti‐head‐to‐head dimer in excellent chemical yield with good quantum efficiency (Φ365 = 0.15). X‐ray crystallographic analysis revealed that the dimer crystallized as a conglomerate of C2 space group. The crystalline dimer precipitated upon irradiation of the monomer in solution, and indirect racemization of the dimer through a reversible photoreaction in solution and selective crystallization simultaneously occurred to give the C2‐chiral dimer in optically active form with up to 80 % ee. Optically active photoproducts could be obtained by simply irradiating achiral materials in solution without an external chiral source.

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Asymmetric transformation by dynamic crystallization of achiral succinimides

Cited by 28 publications

References 31 publications

Solid‐Phase Conversion of Four Stereoisomers into a Single Enantiomer

Solid‐Phase Conversion of Four Stereoisomers into a Single Enantiomer

Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Asymmetric Synthesis Involving Reversible Photodimerization of a Prochiral Flavonoid Followed by Crystallization

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