Reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-pyrrolines
[reaction: see text] Carbamate deprotonation followed by treatment with CuCN.2LiCl affords alpha-(N-carbamoyl)alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give alpha-(N-carbamoyl) allenes via an anti-S(N)2' substitution process. P...
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| Veröffentlicht in: | Journal of organic chemistry 2005-03, Vol.70 (6), p.2109-2119 |
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| container_issue | 6 |
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| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | Dieter, R Karl Chen, Ningyi Yu, Huayun Nice, Lois E Gore, Vinayak K |
| description | [reaction: see text] Carbamate deprotonation followed by treatment with CuCN.2LiCl affords alpha-(N-carbamoyl)alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give alpha-(N-carbamoyl) allenes via an anti-S(N)2' substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific S(N)2' substitution in the absence of severe steric hindrance. The alpha-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Delta(3)-pyrrolines with either AgNO(3) or Ru(3)(CO)(12). |
| format | Article |
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Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific S(N)2' substitution in the absence of severe steric hindrance. The alpha-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Delta(3)-pyrrolines with either AgNO(3) or Ru(3)(CO)(12).</description><identifier>ISSN: 0022-3263</identifier><identifier>PMID: 15760194</identifier><language>eng</language><publisher>United States</publisher><subject>Alkadienes - chemical synthesis ; Alkynes - chemistry ; Copper - chemistry ; Molecular Structure ; Organometallic Compounds - chemical synthesis ; Organometallic Compounds - chemistry ; Propanols - chemistry ; Pyrroles - chemical synthesis</subject><ispartof>Journal of organic chemistry, 2005-03, Vol.70 (6), p.2109-2119</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15760194$$D View this record in MEDLINE/PubMed$$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 alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-pyrrolines</title><title>Journal of organic chemistry</title><addtitle>J Org Chem</addtitle><description>[reaction: see text] Carbamate deprotonation followed by treatment with CuCN.2LiCl affords alpha-(N-carbamoyl)alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give alpha-(N-carbamoyl) allenes via an anti-S(N)2' substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific S(N)2' substitution in the absence of severe steric hindrance. The alpha-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Delta(3)-pyrrolines with either AgNO(3) or Ru(3)(CO)(12).</description><subject>Alkadienes - chemical synthesis</subject><subject>Alkynes - chemistry</subject><subject>Copper - chemistry</subject><subject>Molecular Structure</subject><subject>Organometallic Compounds - chemical synthesis</subject><subject>Organometallic Compounds - chemistry</subject><subject>Propanols - chemistry</subject><subject>Pyrroles - chemical synthesis</subject><issn>0022-3263</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo1kE1LxDAQhnNQ3HX1L0hOoodCmq9uvIn4BYuC7L1M06lbTZuapEjv_nCrrvMeZpj35YGZA7JkjPNMcC0W5DjGNzaXUuqILHJVaJYbuSRfLwg2tb6nvqHghh1kF0-ZhVBB5yd3Ce59cnYcAiSM9LNNOzoEP0B4nRyNYxXTr3NF49SnHabW0uDHhDT5PQ66tv-ZHfYzAfqa1ugSiGyYQvCunbcn5LABF_F031dke3e7vXnINs_3jzfXm2xQUmZ1UynbcK4LqQGN0EZzXDPTCCUEqwo2a820zWuZN5WUWqCprTE5V8oYXIsVOf_Dzhd8jBhT2bXRonPQox9jqQvFjBb5HDzbB8eqw7ocQttBmMr_t4lvkytqNg</recordid><startdate>20050318</startdate><enddate>20050318</enddate><creator>Dieter, R Karl</creator><creator>Chen, Ningyi</creator><creator>Yu, Huayun</creator><creator>Nice, Lois E</creator><creator>Gore, Vinayak K</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20050318</creationdate><title>Reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-pyrrolines</title><author>Dieter, R Karl ; Chen, Ningyi ; Yu, Huayun ; Nice, Lois E ; Gore, Vinayak K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p544-dfb5cf226746ae936962e809f35330b70707806c1d41fb4463e9dc99125599e83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Alkadienes - chemical synthesis</topic><topic>Alkynes - chemistry</topic><topic>Copper - chemistry</topic><topic>Molecular Structure</topic><topic>Organometallic Compounds - chemical synthesis</topic><topic>Organometallic Compounds - chemistry</topic><topic>Propanols - chemistry</topic><topic>Pyrroles - chemical synthesis</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>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</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 alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-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><abstract>[reaction: see text] Carbamate deprotonation followed by treatment with CuCN.2LiCl affords alpha-(N-carbamoyl)alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give alpha-(N-carbamoyl) allenes via an anti-S(N)2' substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific S(N)2' substitution in the absence of severe steric hindrance. The alpha-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Delta(3)-pyrrolines with either AgNO(3) or Ru(3)(CO)(12).</abstract><cop>United States</cop><pmid>15760194</pmid><tpages>11</tpages></addata></record> |
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| subjects | Alkadienes - chemical synthesis Alkynes - chemistry Copper - chemistry Molecular Structure Organometallic Compounds - chemical synthesis Organometallic Compounds - chemistry Propanols - chemistry Pyrroles - chemical synthesis |
| title | Reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-pyrrolines |
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