Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide
Distilled propargyltrichlorosilane with >99% isomeric purity was prepared for the first time, and its asymmetric catalytic regiospecific addition reaction to aldehydes was developed through a systematic catalyst structure–reactivity and selectivity relationship study. The observed catalyst struct...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2024-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.20.255 |
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| author | Noble Brako Sreerag Moorkkannur Narayanan Amber Burns Layla Auter Valentino Cesiliano Rajeev Prabhakar Norito Takenaka |
| author_facet | Noble Brako Sreerag Moorkkannur Narayanan Amber Burns Layla Auter Valentino Cesiliano Rajeev Prabhakar Norito Takenaka |
| author_sort | Noble Brako |
| collection | DOAJ |
| description | Distilled propargyltrichlorosilane with >99% isomeric purity was prepared for the first time, and its asymmetric catalytic regiospecific addition reaction to aldehydes was developed through a systematic catalyst structure–reactivity and selectivity relationship study. The observed catalyst structure–enantioselectivity relationship of the present allenylation reaction was found exactly opposite to that of the analogous allylation reaction. The method provided eleven α-allenic alcohols in 22–99% yield with 61:39–92:8 enantiomeric ratios. Furthermore, possible mechanisms of propargyl–allenyl isomerization of propargyltrichlorosilane were computationally investigated. |
| format | Article |
| id | doaj-art-c31569bb2cb64c9b98b4604a81f877c7 |
| institution | DOAJ |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-c31569bb2cb64c9b98b4604a81f877c72025-08-20T02:51:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-11-012013069307610.3762/bjoc.20.2551860-5397-20-255Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxideNoble Brako0Sreerag Moorkkannur Narayanan1Amber Burns2Layla Auter3Valentino Cesiliano4Rajeev Prabhakar5Norito Takenaka6Department of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, USA Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33146-0431, USA Department of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, USA Department of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, USA Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33146-0431, USA Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33146-0431, USA Department of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, USA Distilled propargyltrichlorosilane with >99% isomeric purity was prepared for the first time, and its asymmetric catalytic regiospecific addition reaction to aldehydes was developed through a systematic catalyst structure–reactivity and selectivity relationship study. The observed catalyst structure–enantioselectivity relationship of the present allenylation reaction was found exactly opposite to that of the analogous allylation reaction. The method provided eleven α-allenic alcohols in 22–99% yield with 61:39–92:8 enantiomeric ratios. Furthermore, possible mechanisms of propargyl–allenyl isomerization of propargyltrichlorosilane were computationally investigated.https://doi.org/10.3762/bjoc.20.255α-allenic alcoholcomputational chemistrylewis base catalysisorganocatalysispropargyltrichlorosilane |
| spellingShingle | Noble Brako Sreerag Moorkkannur Narayanan Amber Burns Layla Auter Valentino Cesiliano Rajeev Prabhakar Norito Takenaka Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide Beilstein Journal of Organic Chemistry α-allenic alcohol computational chemistry lewis base catalysis organocatalysis propargyltrichlorosilane |
| title | Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide |
| title_full | Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide |
| title_fullStr | Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide |
| title_full_unstemmed | Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide |
| title_short | Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide |
| title_sort | enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline n n dioxide |
| topic | α-allenic alcohol computational chemistry lewis base catalysis organocatalysis propargyltrichlorosilane |
| url | https://doi.org/10.3762/bjoc.20.255 |
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