Crystallization Induced Dynamic Resolution of Ethyl Thiazolidine-2-Carboxylate

Kang, Seung Kyu; Park, Woul Seong; Thopate, T. S.; Ahn, Jin Hee

doi:10.5012/bkcs.2010.31.9.2709

Cited by 3 publications

(1 citation statement)

References 12 publications

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“…Similarly, as investigated by Ahn et al., ( S )‐ethyl thiazolidine‐2‐carboxylate 87 undergoes a rapid racemization if heated at 80 °C with L‐TA in ethanol (Scheme 32). [84] On the other hand, after 24 h at rt racemization of ( S )‐ 87 remained undetectable. For the sake of productive CIDT of rac ‐ 87 it appeared optimal to combine cycles of heating (>40 °C) and cooling to rt with a partial evaporation ( ca 30%) of ethanol/ether (3:1 v/v), which was used as the solvent.…”

Section: Examples Of Cidtmentioning

confidence: 99%

State of the Art in Crystallization‐Induced Diastereomer Transformations

Kolarovič

Jakubec

2021

Adv Synth Catal

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Crystallization-induced diastereomer transformations (CIDT) enable isolation of the target compounds in high enantio-and diastereomeric purities and with up to quantitative yields simply by filtration. Numerous inspiring examples of this appealing synthetic strategy reported over the last fifteen years are reviewed. Important observations along with aspects to consider when designing CIDT experiments are discussed. 3.3. Formation of Schiff Base or Related Intermediates 3.4. Aza-Michael and Mannich-Type Reactions 3.5. Strecker Reaction 3.6. Aldol Reactions 3.7. Epimerization at Phosphorus-Based Stereocenters 3.8. Racemization/Epimerization through Change of Conformation 3.9. Miscellaneous Examples of CIDT 4.Conclusions and Perspectives

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Section: Examples Of Cidtmentioning

confidence: 99%