Asymmetric Organocatalytic Allylic Substitution of Morita–Baylis–Hillman Carbonates with Allylamines for the Synthesis of 2,5-Dihydropyrroles
The asymmetric allylic substitution reaction of MBH carbonates with allylamines has been developed, which affords N-allyl-β-amino-α-methylene esters in high yields and enantioselectivities. After a subsequent ring-closure metathesis of the products, a series of optically active 2,5-dihydropyrroles c...
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| Veröffentlicht in: | Journal of organic chemistry 2011-10, Vol.76 (19), p.7826-7833 |
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| container_end_page | 7833 |
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| container_issue | 19 |
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| container_title | Journal of organic chemistry |
| container_volume | 76 |
| creator | Sun, Wangsheng Ma, Xiaozhou Hong, Liang Wang, Rui |
| description | The asymmetric allylic substitution reaction of MBH carbonates with allylamines has been developed, which affords N-allyl-β-amino-α-methylene esters in high yields and enantioselectivities. After a subsequent ring-closure metathesis of the products, a series of optically active 2,5-dihydropyrroles could be obtained smoothly in high yields without any loss of enantioselectivity. Finally, a tentative mechanism for rationalization of the reaction has been proposed. |
| doi_str_mv | 10.1021/jo2011522 |
| format | Article |
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After a subsequent ring-closure metathesis of the products, a series of optically active 2,5-dihydropyrroles could be obtained smoothly in high yields without any loss of enantioselectivity. Finally, a tentative mechanism for rationalization of the reaction has been proposed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo2011522</identifier><identifier>PMID: 21812473</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkenes - chemistry ; Allylamine - chemistry ; Carbonates - chemistry ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Kinetics and mechanisms ; Organic chemistry ; Preparations and properties ; Pyrroles - chemical synthesis ; Pyrroles - chemistry ; Reactivity and mechanisms ; Stereoisomerism ; Substrate Specificity ; Theory of reactions, general kinetics. Catalysis. 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Org. Chem</addtitle><description>The asymmetric allylic substitution reaction of MBH carbonates with allylamines has been developed, which affords N-allyl-β-amino-α-methylene esters in high yields and enantioselectivities. After a subsequent ring-closure metathesis of the products, a series of optically active 2,5-dihydropyrroles could be obtained smoothly in high yields without any loss of enantioselectivity. Finally, a tentative mechanism for rationalization of the reaction has been proposed.</description><subject>Alkenes - chemistry</subject><subject>Allylamine - chemistry</subject><subject>Carbonates - chemistry</subject><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 only one n hetero atom and condensed derivatives</subject><subject>Kinetics and mechanisms</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Reactivity and mechanisms</subject><subject>Stereoisomerism</subject><subject>Substrate Specificity</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkcFu1DAQhq0K1G4Lh75AlQuqKhGwnTgbH7cLpUhFe1g4RxPH6bpy7MXjCOXWV0C8IU-Cl92WC778nplP_y_NEHLO6DtGOXv_4DllTHB-RGZJaF5JWr4gM0o5zwteFSfkFPGBpieEOCYnnNWMl_NiRn4ucBoGHYNR2Srcg_MKItgppnph7WSTrscWo4ljNN5lvs---GAi_H78dQ1pjulza6wdwGVLCK13EDVmP0zc7B1gMC41eh-yuNHZenJJ0ODOir8V-Qezmbrgt1MI3mp8RV72YFG_PugZ-Xbz8evyNr9bffq8XNzlUJRlzDmVVS87UdXAtZKykKyTNadCMaHaqpBAadlWTAg2r4RmrJv3XFIx71jH-k4WZ-Ry77sN_vuoMTaDQaWtBaf9iE0tRS1qXtFEXu1JFTxi0H2zDWaAMDWMNrsDNM8HSOzFwXVsB909k08bT8CbAwCowPYBnDL4jyt3qX9DDxwoTP5jcGkZ_wn8AwownG8</recordid><startdate>20111007</startdate><enddate>20111007</enddate><creator>Sun, Wangsheng</creator><creator>Ma, Xiaozhou</creator><creator>Hong, Liang</creator><creator>Wang, Rui</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20111007</creationdate><title>Asymmetric Organocatalytic Allylic Substitution of Morita–Baylis–Hillman Carbonates with Allylamines for the Synthesis of 2,5-Dihydropyrroles</title><author>Sun, Wangsheng ; Ma, Xiaozhou ; Hong, Liang ; Wang, Rui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-2096f9d568a2ec99391d98205c15cb639a004b61551765e11d7f29057d1d1fd93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alkenes - chemistry</topic><topic>Allylamine - chemistry</topic><topic>Carbonates - chemistry</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Kinetics and mechanisms</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Reactivity and mechanisms</topic><topic>Stereoisomerism</topic><topic>Substrate Specificity</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Wangsheng</creatorcontrib><creatorcontrib>Ma, Xiaozhou</creatorcontrib><creatorcontrib>Hong, Liang</creatorcontrib><creatorcontrib>Wang, Rui</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</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>Sun, Wangsheng</au><au>Ma, Xiaozhou</au><au>Hong, Liang</au><au>Wang, Rui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Organocatalytic Allylic Substitution of Morita–Baylis–Hillman Carbonates with Allylamines for the Synthesis of 2,5-Dihydropyrroles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2011-10-07</date><risdate>2011</risdate><volume>76</volume><issue>19</issue><spage>7826</spage><epage>7833</epage><pages>7826-7833</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The asymmetric allylic substitution reaction of MBH carbonates with allylamines has been developed, which affords N-allyl-β-amino-α-methylene esters in high yields and enantioselectivities. After a subsequent ring-closure metathesis of the products, a series of optically active 2,5-dihydropyrroles could be obtained smoothly in high yields without any loss of enantioselectivity. Finally, a tentative mechanism for rationalization of the reaction has been proposed.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>21812473</pmid><doi>10.1021/jo2011522</doi><tpages>8</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2011-10, Vol.76 (19), p.7826-7833 |
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| source | MEDLINE; American Chemical Society (ACS) Journals |
| subjects | Alkenes - chemistry Allylamine - chemistry Carbonates - chemistry Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Organic chemistry Preparations and properties Pyrroles - chemical synthesis Pyrroles - chemistry Reactivity and mechanisms Stereoisomerism Substrate Specificity Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Asymmetric Organocatalytic Allylic Substitution of Morita–Baylis–Hillman Carbonates with Allylamines for the Synthesis of 2,5-Dihydropyrroles |
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