Palladium-Catalyzed Intramolecular Asymmetric Hydroamination, Hydroalkoxylation, and Hydrocarbonation of Alkynes
A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd2(dba)3·CHCl3/PhCOOH/renorphos 4 i...
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| Veröffentlicht in: | Journal of organic chemistry 2006-05, Vol.71 (11), p.4270-4279 |
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| container_end_page | 4279 |
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| container_issue | 11 |
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| container_title | Journal of organic chemistry |
| container_volume | 71 |
| creator | Patil, Nitin T Lutete, Léopold Mpaka Wu, Huanyou Pahadi, Nirmal K Gridnev, Ilya D Yamamoto, Yoshinori |
| description | A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd2(dba)3·CHCl3/PhCOOH/renorphos 4 in benzene (or benzene−hexane) at 100 °C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations. |
| doi_str_mv | 10.1021/jo0603835 |
| format | Article |
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The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd2(dba)3·CHCl3/PhCOOH/renorphos 4 in benzene (or benzene−hexane) at 100 °C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0603835</identifier><identifier>PMID: 16709071</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Catalysis ; Catalysts: preparations and properties ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties ; Theory of reactions, general kinetics. Catalysis. 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Org. Chem</addtitle><description>A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd2(dba)3·CHCl3/PhCOOH/renorphos 4 in benzene (or benzene−hexane) at 100 °C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations.</description><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Theory of reactions, general kinetics. Catalysis. 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Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Patil, Nitin T</creatorcontrib><creatorcontrib>Lutete, Léopold Mpaka</creatorcontrib><creatorcontrib>Wu, Huanyou</creatorcontrib><creatorcontrib>Pahadi, Nirmal K</creatorcontrib><creatorcontrib>Gridnev, Ilya D</creatorcontrib><creatorcontrib>Yamamoto, Yoshinori</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Patil, Nitin T</au><au>Lutete, Léopold Mpaka</au><au>Wu, Huanyou</au><au>Pahadi, Nirmal K</au><au>Gridnev, Ilya D</au><au>Yamamoto, Yoshinori</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Intramolecular Asymmetric Hydroamination, Hydroalkoxylation, and Hydrocarbonation of Alkynes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2006-05-26</date><risdate>2006</risdate><volume>71</volume><issue>11</issue><spage>4270</spage><epage>4279</epage><pages>4270-4279</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd2(dba)3·CHCl3/PhCOOH/renorphos 4 in benzene (or benzene−hexane) at 100 °C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16709071</pmid><doi>10.1021/jo0603835</doi><tpages>10</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2006-05, Vol.71 (11), p.4270-4279 |
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| source | ACS Publications |
| subjects | Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Palladium-Catalyzed Intramolecular Asymmetric Hydroamination, Hydroalkoxylation, and Hydrocarbonation of Alkynes |
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