Reaction of α-(N-Carbamoyl)alkylcuprates with Propargyl Substrates: Synthetic Route to α-Amino Allenes and Δ3-Pyrrolines
Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2‘ substitution process. Propargyl halides, sulfonates, and ph...
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| Veröffentlicht in: | Journal of organic chemistry 2005-03, Vol.70 (6), p.2109-2119 |
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| container_end_page | 2119 |
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| container_issue | 6 |
| container_start_page | 2109 |
| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | Dieter, R. Karl Chen, Ningyi Yu, Huayun Nice, Lois E. Gore, Vinayak K. |
| description | Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2‘ substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific SN2‘ substitution in the absence of severe steric hindrance. The α-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Δ3-pyrrolines with either AgNO3 or Ru3(CO)12. |
| doi_str_mv | 10.1021/jo0481405 |
| format | Article |
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Karl ; Chen, Ningyi ; Yu, Huayun ; Nice, Lois E. ; Gore, Vinayak K.</creator><creatorcontrib>Dieter, R. Karl ; Chen, Ningyi ; Yu, Huayun ; Nice, Lois E. ; Gore, Vinayak K.</creatorcontrib><description>Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2‘ substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific SN2‘ substitution in the absence of severe steric hindrance. The α-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Δ3-pyrrolines with either AgNO3 or Ru3(CO)12.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0481405</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2005-03, Vol.70 (6), p.2109-2119</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo0481405$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0481405$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16617303$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Dieter, R. Karl</creatorcontrib><creatorcontrib>Chen, Ningyi</creatorcontrib><creatorcontrib>Yu, Huayun</creatorcontrib><creatorcontrib>Nice, Lois E.</creatorcontrib><creatorcontrib>Gore, Vinayak K.</creatorcontrib><title>Reaction of α-(N-Carbamoyl)alkylcuprates with Propargyl Substrates: Synthetic Route to α-Amino Allenes and Δ3-Pyrrolines</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2‘ substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific SN2‘ substitution in the absence of severe steric hindrance. The α-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Δ3-pyrrolines with either AgNO3 or Ru3(CO)12.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpFkc2O0zAUhS3ESJQOC97AGyRYmPFP4iTsSgeYkaqhaiMhdWPdOA5Nx40j2xVkg9iy50XmRfoQPAnpDBrO5krnHH3S1UHoJaNvGeXsYudokrOEpk_QhKWcElnQ5CmaUMo5EVyKZ-h5CDs6Kk3TCfqxMqBj6zrsGny8I69vyBx8BXs32DdgbwerD72HaAL-1sYtXnrXg_86WLw-VCHeJ-_-_PyF10MXtya2Gq_cIRoc3Qk327edwzNrTTcSoKvx8bcgy8F7Z9vROkdnDdhgXvy7U1R-_FDOr8ji86fr-WxBoMgF0XWd13WRZTXPeSFyw4qqbiAxIDRkeZKkDTfcgJF5zSEpdNUUVZZnrOJSFiDEFL16wPYQNNjGQ6fboHrf7sEPiknJMkFPPfLQa0M03x9z8LdKZiJLVblcK_n-y2Z5STeq_M8FHdTOHXw3PqEYVact1OMW4i9-Cn-C</recordid><startdate>20050318</startdate><enddate>20050318</enddate><creator>Dieter, R. 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Karl ; Chen, Ningyi ; Yu, Huayun ; Nice, Lois E. ; Gore, Vinayak K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a983-cdd8dd977d282938e19bdfa4ea3ca78445f2e2eae68d2a49cbf9b7871b2669a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dieter, R. Karl</creatorcontrib><creatorcontrib>Chen, Ningyi</creatorcontrib><creatorcontrib>Yu, Huayun</creatorcontrib><creatorcontrib>Nice, Lois E.</creatorcontrib><creatorcontrib>Gore, Vinayak K.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dieter, R. Karl</au><au>Chen, Ningyi</au><au>Yu, Huayun</au><au>Nice, Lois E.</au><au>Gore, Vinayak K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reaction of α-(N-Carbamoyl)alkylcuprates with Propargyl Substrates: Synthetic Route to α-Amino Allenes and Δ3-Pyrrolines</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-03-18</date><risdate>2005</risdate><volume>70</volume><issue>6</issue><spage>2109</spage><epage>2119</epage><pages>2109-2119</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2‘ substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific SN2‘ substitution in the absence of severe steric hindrance. The α-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Δ3-pyrrolines with either AgNO3 or Ru3(CO)12.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/jo0481405</doi><tpages>11</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2005-03, Vol.70 (6), p.2109-2119 |
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| language | eng |
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| source | ACS Publications |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Reaction of α-(N-Carbamoyl)alkylcuprates with Propargyl Substrates: Synthetic Route to α-Amino Allenes and Δ3-Pyrrolines |
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