Highly enantio-, regio- and diastereo-selective one-pot [2 + 3]-cycloaddition reaction via isomerization of 3-butynoates to allenoatesElectronic supplementary information (ESI) available: Detailed experimental procedures and analytical data. CCDC reference number 748921. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c0sc00123f, General procedure for the synthesis of 2a: To a stirred solution of 3-butynoate 1a (50 mg; 0.265 mmol) and trans-chalcone (61 mg, 0
Phosphine-catalyzed one-pot isomerization and [2 + 3]-cycloaddition of 3-butynoates with electron-deficient olefins affords highly functionalized cyclopentenes with both good yields and excellent selectivities of up to 99%. Phosphine-catalyzed one-pot isomerization and [2 + 3]-cycloaddition of 3-but...
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| Main Authors | , |
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| Format | Journal Article |
| Language | English |
| Published |
08.11.2010
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| Online Access | Get full text |
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| Summary: | Phosphine-catalyzed one-pot isomerization and [2 + 3]-cycloaddition of 3-butynoates with electron-deficient olefins affords highly functionalized cyclopentenes with both good yields and excellent selectivities of up to 99%.
Phosphine-catalyzed one-pot isomerization and [2 + 3]-cycloaddition of 3-butynoates with electron-deficient olefins affords highly functionalized cyclopentenes with both good yields and excellent selectivities of up to 99%. |
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| Bibliography: | atmosphere, the reaction mixture was concentrated and purified using flash column chromatography (10% ethyl acetate in hexane) to afford pure product 10.1039/c0sc00123f (89.5 mg, 87% yield, 95% ee). chalcone (61 mg, 0.292 mmol) in toluene (1.5 mL) was added , 748921 To a stirred solution of 3-butynoate 2a Electronic supplementary information (ESI) available: Detailed experimental procedures and analytical data. CCDC reference number 1a For ESI and crystallographic data in CIF or other electronic format see DOI 2 DIPAMP) (12 mg, 0.026 mmol; pre-dissolved in toluene) dropwise at 0 °C under nitrogen. After 8 h stirring at room temperature under N R General procedure for the synthesis of (50 mg; 0.265 mmol) and trans |
| ISSN: | 2041-6520 2041-6539 |
| DOI: | 10.1039/c0sc00123f |