Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives
Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts in high yield (up to 94%) and excellent enant...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.91 |
| _version_ | 1818621455080882176 |
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| author | Akshay Kumar Swapandeep Singh Chimni |
| author_facet | Akshay Kumar Swapandeep Singh Chimni |
| author_sort | Akshay Kumar |
| collection | DOAJ |
| description | Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts in high yield (up to 94%) and excellent enantioselectivity (up to 99%). The catalyst 1a was successfully used to catalyze the three-component version of the reaction by a domino Knoevenagel–Michael sequence. The Michael adduct 4a was transformed into spirooxindole 6 by a reduction with sodium borohydride in a highly enantioselective manner. |
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| format | Article |
| id | doaj.art-fdd3be4d359b44dba3821cca0bc6bd60 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T18:09:32Z |
| publishDate | 2014-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-fdd3be4d359b44dba3821cca0bc6bd602022-12-21T22:21:49ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-04-0110192993510.3762/bjoc.10.911860-5397-10-91Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivativesAkshay Kumar0Swapandeep Singh Chimni1Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, 143005, India; Fax: (+)91-183-2258820Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, 143005, India; Fax: (+)91-183-2258820Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts in high yield (up to 94%) and excellent enantioselectivity (up to 99%). The catalyst 1a was successfully used to catalyze the three-component version of the reaction by a domino Knoevenagel–Michael sequence. The Michael adduct 4a was transformed into spirooxindole 6 by a reduction with sodium borohydride in a highly enantioselective manner.https://doi.org/10.3762/bjoc.10.913,3'-disubstituted oxindolesMichael reactionorganocatalysisprimary-tertiary diaminespirooxindoles |
| spellingShingle | Akshay Kumar Swapandeep Singh Chimni Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives Beilstein Journal of Organic Chemistry 3,3'-disubstituted oxindoles Michael reaction organocatalysis primary-tertiary diamine spirooxindoles |
| title | Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives |
| title_full | Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives |
| title_fullStr | Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives |
| title_full_unstemmed | Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives |
| title_short | Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives |
| title_sort | primary tertiary diamine catalyzed michael addition of ketones to isatylidenemalononitrile derivatives |
| topic | 3,3'-disubstituted oxindoles Michael reaction organocatalysis primary-tertiary diamine spirooxindoles |
| url | https://doi.org/10.3762/bjoc.10.91 |
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