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An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement
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| Zeitschriftentitel: | Angewandte Chemie International Edition |
|---|---|
| Personen und Körperschaften: | , , , , , |
| In: | Angewandte Chemie International Edition, 56, 2017, 8, S. 2212-2215 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Kaldre, Dainis Maryasin, Boris Kaiser, Daniel Gajsek, Oliver González, Leticia Maulide, Nuno Kaldre, Dainis Maryasin, Boris Kaiser, Daniel Gajsek, Oliver González, Leticia Maulide, Nuno |
|---|---|
| author |
Kaldre, Dainis Maryasin, Boris Kaiser, Daniel Gajsek, Oliver González, Leticia Maulide, Nuno |
| spellingShingle |
Kaldre, Dainis Maryasin, Boris Kaiser, Daniel Gajsek, Oliver González, Leticia Maulide, Nuno Angewandte Chemie International Edition An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement General Chemistry Catalysis |
| author_sort |
kaldre, dainis |
| spelling |
Kaldre, Dainis Maryasin, Boris Kaiser, Daniel Gajsek, Oliver González, Leticia Maulide, Nuno 1433-7851 1521-3773 Wiley General Chemistry Catalysis http://dx.doi.org/10.1002/anie.201610105 <jats:title>Abstract</jats:title><jats:p>A general, asymmetric redox arylation of ynamides and thioalkynes with chiral sulfoxides is reported. This is the first example of a general 1,4‐chirality transfer from sulfur to a carbon stereocenter through a sulfonium [3,3]‐sigmatropic rearrangement. This reaction delivers α‐arylated thioesters and amides under mild conditions in an atom‐economical manner. The products are formed in high yields with enantiomeric ratios up to 99.5:0.5. Quantum chemical calculations suggest a mechanism for the chirality transfer from sulfur to carbon and explain the experimentally observed correlation of the enantioselectivity with both the catalyst and the substrate.</jats:p> An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement Angewandte Chemie International Edition |
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10.1002/anie.201610105 |
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| title |
An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_unstemmed |
An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_full |
An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_fullStr |
An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_full_unstemmed |
An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_short |
An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_sort |
an asymmetric redox arylation: chirality transfer from sulfur to carbon through a sulfonium [3,3]‐sigmatropic rearrangement |
| topic |
General Chemistry Catalysis |
| url |
http://dx.doi.org/10.1002/anie.201610105 |
| publishDate |
2017 |
| physical |
2212-2215 |
| description |
<jats:title>Abstract</jats:title><jats:p>A general, asymmetric redox arylation of ynamides and thioalkynes with chiral sulfoxides is reported. This is the first example of a general 1,4‐chirality transfer from sulfur to a carbon stereocenter through a sulfonium [3,3]‐sigmatropic rearrangement. This reaction delivers α‐arylated thioesters and amides under mild conditions in an atom‐economical manner. The products are formed in high yields with enantiomeric ratios up to 99.5:0.5. Quantum chemical calculations suggest a mechanism for the chirality transfer from sulfur to carbon and explain the experimentally observed correlation of the enantioselectivity with both the catalyst and the substrate.</jats:p> |
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| author | Kaldre, Dainis, Maryasin, Boris, Kaiser, Daniel, Gajsek, Oliver, González, Leticia, Maulide, Nuno |
| author_facet | Kaldre, Dainis, Maryasin, Boris, Kaiser, Daniel, Gajsek, Oliver, González, Leticia, Maulide, Nuno, Kaldre, Dainis, Maryasin, Boris, Kaiser, Daniel, Gajsek, Oliver, González, Leticia, Maulide, Nuno |
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| description | <jats:title>Abstract</jats:title><jats:p>A general, asymmetric redox arylation of ynamides and thioalkynes with chiral sulfoxides is reported. This is the first example of a general 1,4‐chirality transfer from sulfur to a carbon stereocenter through a sulfonium [3,3]‐sigmatropic rearrangement. This reaction delivers α‐arylated thioesters and amides under mild conditions in an atom‐economical manner. The products are formed in high yields with enantiomeric ratios up to 99.5:0.5. Quantum chemical calculations suggest a mechanism for the chirality transfer from sulfur to carbon and explain the experimentally observed correlation of the enantioselectivity with both the catalyst and the substrate.</jats:p> |
| doi_str_mv | 10.1002/anie.201610105 |
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| imprint | Wiley, 2017 |
| imprint_str_mv | Wiley, 2017 |
| institution | DE-15, DE-Rs1, DE-Pl11, DE-105, DE-14, DE-Ch1, DE-L229, DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4 |
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| issn_str_mv | 1433-7851, 1521-3773 |
| language | English |
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| physical | 2212-2215 |
| publishDate | 2017 |
| publishDateSort | 2017 |
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| series | Angewandte Chemie International Edition |
| source_id | 49 |
| spelling | Kaldre, Dainis Maryasin, Boris Kaiser, Daniel Gajsek, Oliver González, Leticia Maulide, Nuno 1433-7851 1521-3773 Wiley General Chemistry Catalysis http://dx.doi.org/10.1002/anie.201610105 <jats:title>Abstract</jats:title><jats:p>A general, asymmetric redox arylation of ynamides and thioalkynes with chiral sulfoxides is reported. This is the first example of a general 1,4‐chirality transfer from sulfur to a carbon stereocenter through a sulfonium [3,3]‐sigmatropic rearrangement. This reaction delivers α‐arylated thioesters and amides under mild conditions in an atom‐economical manner. The products are formed in high yields with enantiomeric ratios up to 99.5:0.5. Quantum chemical calculations suggest a mechanism for the chirality transfer from sulfur to carbon and explain the experimentally observed correlation of the enantioselectivity with both the catalyst and the substrate.</jats:p> An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement Angewandte Chemie International Edition |
| spellingShingle | Kaldre, Dainis, Maryasin, Boris, Kaiser, Daniel, Gajsek, Oliver, González, Leticia, Maulide, Nuno, Angewandte Chemie International Edition, An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement, General Chemistry, Catalysis |
| title | An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_full | An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_fullStr | An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_full_unstemmed | An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_short | An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| title_sort | an asymmetric redox arylation: chirality transfer from sulfur to carbon through a sulfonium [3,3]‐sigmatropic rearrangement |
| title_unstemmed | An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]‐Sigmatropic Rearrangement |
| topic | General Chemistry, Catalysis |
| url | http://dx.doi.org/10.1002/anie.201610105 |