Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, Second Edition

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In contrast to the strategy shown in Scheme 2 toward the same synthesis target,12 Michael acceptor 98, in this case, was used as the alkylation reagent instead of its surrogate 1,3-dichlorobutene 8. The critical step of the process route is an enantioselective Michael addition of indanone to set the all-carbon quaternary stereogenic center.

This scalable synthetic route was demonstrated at 14 kg scale. Later, the asymmetric synthesis of structurally similar compound was reported by Toyama and co-workers also at Nissan Chemical Industries, Ltd. Figure 5. Structures of 3,5-diaryl trifluoromethyl isoxazolines Scheme The same challenge also applied to the asymmetric phase transfer catalyzed conjugate addition. For instance, the intramolecular oxo-1,4-conjugate addition reaction of under phase transfer conditions reported by Wilhelm and co-workers in required a stoichiometric amount of cinchona alkaloid-based ammonium salt 14a in order to achieve good levels of enantioselectivities Scheme Intramolecular oxo-Michael addition reaction However, recent reports have shown promise that emerging technologies will enable the effective phase transfer-catalyzed intramolecular Michael addition.

In , Humphrey and co-workers at Merck reported a catalytic intramolecular enantioselective aza-Michael addition of guanidine for the synthesis of letermovir , a phase III antiviral drug for the treatment of cytomegalovirus CMV infections Scheme This unprecedented aza-Michael addition method enabled the construction of the critical stereogenic center in and served as the cornerstone of the commercial manufacturing process for this product. Intramolecular conjugate addition reaction of guanidine en route to 4.

In , Rusinov and Chertorizhskii reported highly efficient phase transfercatalyzed epoxidations of steroid derivatives and Scheme This methodology was further applied to the synthesis of Mifeprex , mifepristone ,65 which was originally developed by Roussel Uclaf as a synthetic steroid compound with both antiprogesterone and antiglucocorticoid properties. Asymmetric phase transfer-catalyzed epoxidation reaction 5. The expansion of reaction type is another factor that would be very beneficial for largescale applications. For instance, in , Tamura and Ryukoku in Nippon Chemical Industrial reported the unprecedented phase transfer-catalyzed deracemization reaction for the synthesis of chiral phosphorous amides , which is a potent insecticide, miticide and nematicide Scheme This method constitutes a synthetic alternative to classical resolution methods.

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Although the reaction mechanism is not clear and the reported enantioselectivity is modest, this discovery may still open a new direction for expanding the scope of asymmetric phase transfer catalysis. Asymmetric synthesis of phosphorous amide 6. This protocol has been further demonstrated at gram scale. Although an enzyme-based asymmetric synthesis was later developed and utilized as the optimal manufacturing process for compound ,69 this unique transformation is an example of the opportunities available for expanding the applications of asymmetric phase transfer catalysis.

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Asymmetric phase transfer-catalyzed desymmetrization reaction of compound 7. Synthetic chemists have developed a wide variety of chiral PTCs, such as cinchona alkaloid-based catalysts, Maruoka catalysts, and Denmark catalysts,7 and as the quantity and variety of chiral PTCs have grown so too has the diversity of transformations that can be conducted with them. Accordingly, much work remains to unlock its full potential, and future research must include the development of scalable and cost-efficient methods, the improvement of chiral PTC availability in bulk quantities, the broadening of reaction scope, and the integration of phase transfer catalysis with other catalytic manifolds.

Acknowledgement We gratefully acknowledged the help from Dr. Michael Kress, Dr. Kevin Campos, Dr. Feng Xu, Dr.


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Guy Humphrey, Bangping Xiang, Dr. Zhijian Liu, Dr. David Thaisrivongs, Dr. Artis Klapars, Dr. Paul Bulger, Dr. Rebecca Ruck, Dr. Mark Huffman, Dr. Jacob Waldman and Dr. Alexie Kalinin. Reference: 1 Starks, C. Pure Appl. Phase Transfer Catalysis, 3rd Ed. Pure and Appl. Asymmetric Organocatalysis; Springer: New York, Comprehensive Enantioselective Organocatalysis, Vols. Catalytic Asymmetric Synthesis; Ojima, I. Aldrichimica Acta , 34, 3. Aldrichimica Acta , 40, Tetrahedron , 70, Comprehensive Chirality: Volume 9; Carreira, E.

A manipulated enantiomer mixture by asymmetric chiral phase transfer catalysts. EP , Labelled Compd. Drug Metab.

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Asymmetric Synthesis

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Contemporary Asymmetric Phase Transfer Catalysis: Large-Scale - PDF Free Download

Described in I. Ojima, N. Clos, C. Bastos, Tetrahedron , 45, Rasor, E. Voss, Appl.

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