Practical Considerations in Kinetic Resolution Reactions

Advanced Synthesis and Catalysis

Volumn 343, Issue 1, 2001, Pages 5-26

  Keith, John M ^a   Larrow, Jay F ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Catalysts; Chiral resolution; Enantiomeric resolution; Epoxidations; Homogeneous catalysis

Indexed keywords

EID: 0002178750     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010129)343:1<5::AID-ADSC5>3.0.CO;2-I     Document Type: Review

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7. This is driven home by the recent example of Crixivan®, the HIV-protease inhibitor drug developed by Merck. Although it served as inspiration for a large body of exciting research in asymmetric catalysis, in the end its commercial synthesis relies on the use of two classical resolutions and three diastereoselective reactions. See: P. J. Reider, Chimia 1997, 51, 306-308.
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12. It is not uncommon for the ee of the product of an enantioselective transformation to change during the course of reaction, particularly in the late stages. This is often encountered when catalyst undergoes decomposition to a species that is still catalytically active, but poorly-or non-enantioselective. Other factors that can lead to changing ee's include alteration of catalyst due to coordination of the chiral product, or subsequent reaction of product in a kinetic resolution manifold. However, these all can be viewed as secondary pathways outside of the principal enantioselective reactive manifold.
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