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Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins
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| Zeitschriftentitel: | Chemistry – A European Journal |
|---|---|
| Personen und Körperschaften: | , , |
| In: | Chemistry – A European Journal, 20, 2014, 33, S. 10519-10526 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Pagar, Vinayak Vishnu Tseng, Chang‐Chin Liu, Rai‐Shung Pagar, Vinayak Vishnu Tseng, Chang‐Chin Liu, Rai‐Shung |
|---|---|
| author |
Pagar, Vinayak Vishnu Tseng, Chang‐Chin Liu, Rai‐Shung |
| spellingShingle |
Pagar, Vinayak Vishnu Tseng, Chang‐Chin Liu, Rai‐Shung Chemistry – A European Journal Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins General Chemistry Catalysis Organic Chemistry |
| author_sort |
pagar, vinayak vishnu |
| spelling |
Pagar, Vinayak Vishnu Tseng, Chang‐Chin Liu, Rai‐Shung 0947-6539 1521-3765 Wiley General Chemistry Catalysis Organic Chemistry http://dx.doi.org/10.1002/chem.201403285 <jats:title>Abstract</jats:title><jats:p>Oxa‐Povarov reactions involving readily available diaryloxymethylarenes and aryl‐substituted alkenes are reported. Their [4+2] cycloadditions were efficiently catalyzed by IPrAuSbF<jats:sub>6</jats:sub> (IPr=1,3‐bis(diisopropylphenyl)imidazol‐2‐ylidene) with high diastereoselectivity. Product analysis revealed that the reactions likely proceed by a stepwise ionic mechanism, because both <jats:italic>E</jats:italic>‐ and <jats:italic>Z</jats:italic>‐configured β‐methylstyrene gave the same cycloadducts in the same proportions.</jats:p> Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins Chemistry – A European Journal |
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10.1002/chem.201403285 |
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Wiley, 2014 |
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| title |
Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_unstemmed |
Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_full |
Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_fullStr |
Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_full_unstemmed |
Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_short |
Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_sort |
gold‐catalyzed oxa‐povarov reactions for the synthesis of highly substituted dihydrobenzopyrans from diaryloxymethylarenes and olefins |
| topic |
General Chemistry Catalysis Organic Chemistry |
| url |
http://dx.doi.org/10.1002/chem.201403285 |
| publishDate |
2014 |
| physical |
10519-10526 |
| description |
<jats:title>Abstract</jats:title><jats:p>Oxa‐Povarov reactions involving readily available diaryloxymethylarenes and aryl‐substituted alkenes are reported. Their [4+2] cycloadditions were efficiently catalyzed by IPrAuSbF<jats:sub>6</jats:sub> (IPr=1,3‐bis(diisopropylphenyl)imidazol‐2‐ylidene) with high diastereoselectivity. Product analysis revealed that the reactions likely proceed by a stepwise ionic mechanism, because both <jats:italic>E</jats:italic>‐ and <jats:italic>Z</jats:italic>‐configured β‐methylstyrene gave the same cycloadducts in the same proportions.</jats:p> |
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| author | Pagar, Vinayak Vishnu, Tseng, Chang‐Chin, Liu, Rai‐Shung |
| author_facet | Pagar, Vinayak Vishnu, Tseng, Chang‐Chin, Liu, Rai‐Shung, Pagar, Vinayak Vishnu, Tseng, Chang‐Chin, Liu, Rai‐Shung |
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| description | <jats:title>Abstract</jats:title><jats:p>Oxa‐Povarov reactions involving readily available diaryloxymethylarenes and aryl‐substituted alkenes are reported. Their [4+2] cycloadditions were efficiently catalyzed by IPrAuSbF<jats:sub>6</jats:sub> (IPr=1,3‐bis(diisopropylphenyl)imidazol‐2‐ylidene) with high diastereoselectivity. Product analysis revealed that the reactions likely proceed by a stepwise ionic mechanism, because both <jats:italic>E</jats:italic>‐ and <jats:italic>Z</jats:italic>‐configured β‐methylstyrene gave the same cycloadducts in the same proportions.</jats:p> |
| doi_str_mv | 10.1002/chem.201403285 |
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| id | ai-49-aHR0cDovL2R4LmRvaS5vcmcvMTAuMTAwMi9jaGVtLjIwMTQwMzI4NQ |
| imprint | Wiley, 2014 |
| imprint_str_mv | Wiley, 2014 |
| institution | DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229 |
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| language | English |
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| physical | 10519-10526 |
| publishDate | 2014 |
| publishDateSort | 2014 |
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| series | Chemistry – A European Journal |
| source_id | 49 |
| spelling | Pagar, Vinayak Vishnu Tseng, Chang‐Chin Liu, Rai‐Shung 0947-6539 1521-3765 Wiley General Chemistry Catalysis Organic Chemistry http://dx.doi.org/10.1002/chem.201403285 <jats:title>Abstract</jats:title><jats:p>Oxa‐Povarov reactions involving readily available diaryloxymethylarenes and aryl‐substituted alkenes are reported. Their [4+2] cycloadditions were efficiently catalyzed by IPrAuSbF<jats:sub>6</jats:sub> (IPr=1,3‐bis(diisopropylphenyl)imidazol‐2‐ylidene) with high diastereoselectivity. Product analysis revealed that the reactions likely proceed by a stepwise ionic mechanism, because both <jats:italic>E</jats:italic>‐ and <jats:italic>Z</jats:italic>‐configured β‐methylstyrene gave the same cycloadducts in the same proportions.</jats:p> Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins Chemistry – A European Journal |
| spellingShingle | Pagar, Vinayak Vishnu, Tseng, Chang‐Chin, Liu, Rai‐Shung, Chemistry – A European Journal, Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins, General Chemistry, Catalysis, Organic Chemistry |
| title | Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_full | Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_fullStr | Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_full_unstemmed | Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_short | Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| title_sort | gold‐catalyzed oxa‐povarov reactions for the synthesis of highly substituted dihydrobenzopyrans from diaryloxymethylarenes and olefins |
| title_unstemmed | Gold‐Catalyzed Oxa‐Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxymethylarenes and Olefins |
| topic | General Chemistry, Catalysis, Organic Chemistry |
| url | http://dx.doi.org/10.1002/chem.201403285 |