Reversal of Product Configuration in Michael Additions of Lithium Enolates to E- and Z-1-Nitro-1-propene
The lithium enolates of certain aldehydes, ketones and esters are added to E- or Z-nitropropene with stereochemical control by the nitroolefin configuration (products 1-5). The configuration of the major diastereomers of the 2.3-dialkylated 4-nitro-carbonyl derivatives thus obtained in selectivitie...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
1984-08-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9619 |
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| Summary: | The lithium enolates of certain aldehydes, ketones and esters are added to E- or Z-nitropropene with stereochemical control by the nitroolefin configuration (products 1-5). The configuration of the major diastereomers of the 2.3-dialkylated 4-nitro-carbonyl derivatives thus obtained in selectivities of 60:40 to 97:3 was assigned by comparison with literature data and by chemical correlation. Cases, in which no reversal of product configuration can be achieved by switching from E- to Z-nitropropene, are also identified.
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| ISSN: | 0009-4293 2673-2424 |