Collective Synthesis of Basic Carbazole Alkaloids

Markad, Shivaji B.; Argade, Narshinha P.

doi:10.14233/ajomc.2018.ajomc-p99

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Racemization/epimerization Through Change Of Conformation1

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2021

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“…A fascinating and possibly the first example of CIDT proceeding in the solid phase was described by Markad and Argade (Scheme 82). [150] They prepared a solid sample of (À )-epi-claulansine D (215) and serendipitously detected that it cleanly transformed into (À )-claulansine D (216) just on standing at rt for nearly two months. Repetitive experiments with both racemic and enantiomerically pure samples of 215 confirmed their complete conversion to 215 after 30 to 90 days.…”

Section: Racemization/epimerization Through Change Of Conformationmentioning

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: Racemization/epimerization Through Change Of Conformationmentioning

confidence: 99%