Abstract
The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(III)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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4-Butyrolactone / analogs & derivatives
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4-Butyrolactone / chemistry*
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Alkadienes / chemical synthesis*
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Alkadienes / chemistry
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Catalysis
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Epoxy Compounds / chemistry*
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Esters / chemistry*
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Hydrolysis
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Kinetics
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Molecular Structure
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Optical Phenomena
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Organometallic Compounds / chemistry
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Paroxetine / chemical synthesis*
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Paroxetine / chemistry
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Piperidines / chemical synthesis*
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Piperidines / chemistry
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Stereoisomerism
Substances
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6-methyl-4,4,5-trifluorohept-1,5-dien-3-ol
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Alkadienes
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Epoxy Compounds
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Esters
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Organometallic Compounds
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Piperidines
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Ro 67-8867
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Paroxetine
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4-Butyrolactone