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Diastereoselective C-alkylation of aldimines, derived from chiral α-carbon heteroatom-substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines
The one-pot reaction of a chiral aldehyde, p -methoxyaniline or p -fluoroaniline, and triethylborane produces the corresponding alkylated chiral amine with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom in the α-position to the aldehyde. In the cas...
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| Published in: | RSC advances 2023-03, Vol.13 (13), p.8976-8984 |
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| container_end_page | 8984 |
| container_issue | 13 |
| container_start_page | 8976 |
| container_title | RSC advances |
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| creator | Fuentes-Ríos, David Muñoz, Carmen Díaz, Amelia Sarabia, Francisco López-Romero, J. Manuel |
| description | The one-pot reaction of a chiral aldehyde,
p
-methoxyaniline or
p
-fluoroaniline, and triethylborane produces the corresponding alkylated chiral amine with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom in the α-position to the aldehyde. In the case of alkylation of imines derived from chiral aliphatic amines, good yields and moderate to high diastereoselectivity are obtained: yields are significantly better when the preformed imine is used in the reaction with triethyl borane, and diastereoselectivity of the reactions largely depends on the structure of the chiral aliphatic amine. The methodology is successfully applied to the synthesis of romneine, a natural benzylisoquinoline.
The one-pot alkylation of aldimines produces alkylated chiral amines with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom (X) in the α-position to the starting aldehyde. |
| doi_str_mv | 10.1039/d3ra01397a |
| format | article |
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p
-methoxyaniline or
p
-fluoroaniline, and triethylborane produces the corresponding alkylated chiral amine with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom in the α-position to the aldehyde. In the case of alkylation of imines derived from chiral aliphatic amines, good yields and moderate to high diastereoselectivity are obtained: yields are significantly better when the preformed imine is used in the reaction with triethyl borane, and diastereoselectivity of the reactions largely depends on the structure of the chiral aliphatic amine. The methodology is successfully applied to the synthesis of romneine, a natural benzylisoquinoline.
The one-pot alkylation of aldimines produces alkylated chiral amines with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom (X) in the α-position to the starting aldehyde.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d3ra01397a</identifier><identifier>PMID: 36936855</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aldehydes ; Aliphatic amines ; Alkylation ; Chemistry ; Imines ; Stereoselectivity</subject><ispartof>RSC advances, 2023-03, Vol.13 (13), p.8976-8984</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2023</rights><rights>This journal is © The Royal Society of Chemistry 2023 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c388t-7bd258d26c56ea5b386ddb05b7c1debd74c0974c574e2a96031bb4ec9ac4f9553</cites><orcidid>0000-0002-5149-3576 ; 0000-0003-2422-655X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10022415/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10022415/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36936855$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fuentes-Ríos, David</creatorcontrib><creatorcontrib>Muñoz, Carmen</creatorcontrib><creatorcontrib>Díaz, Amelia</creatorcontrib><creatorcontrib>Sarabia, Francisco</creatorcontrib><creatorcontrib>López-Romero, J. Manuel</creatorcontrib><title>Diastereoselective C-alkylation of aldimines, derived from chiral α-carbon heteroatom-substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>The one-pot reaction of a chiral aldehyde,
p
-methoxyaniline or
p
-fluoroaniline, and triethylborane produces the corresponding alkylated chiral amine with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom in the α-position to the aldehyde. In the case of alkylation of imines derived from chiral aliphatic amines, good yields and moderate to high diastereoselectivity are obtained: yields are significantly better when the preformed imine is used in the reaction with triethyl borane, and diastereoselectivity of the reactions largely depends on the structure of the chiral aliphatic amine. The methodology is successfully applied to the synthesis of romneine, a natural benzylisoquinoline.
The one-pot alkylation of aldimines produces alkylated chiral amines with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom (X) in the α-position to the starting aldehyde.</description><subject>Aldehydes</subject><subject>Aliphatic amines</subject><subject>Alkylation</subject><subject>Chemistry</subject><subject>Imines</subject><subject>Stereoselectivity</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkk2L1TAUhosozjDOxr0ScCNix3w0abuSyx2_YEAQXZd8nNqMaXNN0pH6r9z4M_xNpnPH62gWSeA85z3vgbcoHhJ8RjBrXxgWJCasreWd4pjiSpQUi_burf9RcRrjJc5HcEIFuV8cMdEy0XB-XPw8tzImCOAjONDJXgHaltJ9WZxM1k_I90g6Y0c7QXyODIRMGNQHPyI92CAd-vWj1DKozA6QlbxMfizjrGKyaU4Zzv0wLGbt_2bTgFKwkIbFKR_kBGdos9s5q_fjkkdpABSXKT_RxnW-gun74mz0X2c7ebc6eVDc66WLcHrznhSfXr_6uH1bXrx_8267uSg1a5pU1spQ3hgqNBcguWKNMEZhrmpNDChTVxq3-eJ1BVS2AjOiVAW6lbrqW87ZSfFyr7ub1QhGw5Tyyt0u2FGGpfPSdv9WJjt0n_1VRzCmtCKrwtMbhZD9Q0zdaKMG5_Lqfo4drZumwVTgOqNP_kMv_RymvN81VeFW0FXw2Z7SwccYoD-4IbhbI9Gdsw-b60hsMvz4tv8D-icAGXi0B0LUh-rfTLHfvAzCmA</recordid><startdate>20230314</startdate><enddate>20230314</enddate><creator>Fuentes-Ríos, David</creator><creator>Muñoz, Carmen</creator><creator>Díaz, Amelia</creator><creator>Sarabia, Francisco</creator><creator>López-Romero, J. Manuel</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-5149-3576</orcidid><orcidid>https://orcid.org/0000-0003-2422-655X</orcidid></search><sort><creationdate>20230314</creationdate><title>Diastereoselective C-alkylation of aldimines, derived from chiral α-carbon heteroatom-substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines</title><author>Fuentes-Ríos, David ; Muñoz, Carmen ; Díaz, Amelia ; Sarabia, Francisco ; López-Romero, J. Manuel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c388t-7bd258d26c56ea5b386ddb05b7c1debd74c0974c574e2a96031bb4ec9ac4f9553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aldehydes</topic><topic>Aliphatic amines</topic><topic>Alkylation</topic><topic>Chemistry</topic><topic>Imines</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fuentes-Ríos, David</creatorcontrib><creatorcontrib>Muñoz, Carmen</creatorcontrib><creatorcontrib>Díaz, Amelia</creatorcontrib><creatorcontrib>Sarabia, Francisco</creatorcontrib><creatorcontrib>López-Romero, J. Manuel</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fuentes-Ríos, David</au><au>Muñoz, Carmen</au><au>Díaz, Amelia</au><au>Sarabia, Francisco</au><au>López-Romero, J. Manuel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereoselective C-alkylation of aldimines, derived from chiral α-carbon heteroatom-substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2023-03-14</date><risdate>2023</risdate><volume>13</volume><issue>13</issue><spage>8976</spage><epage>8984</epage><pages>8976-8984</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>The one-pot reaction of a chiral aldehyde,
p
-methoxyaniline or
p
-fluoroaniline, and triethylborane produces the corresponding alkylated chiral amine with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom in the α-position to the aldehyde. In the case of alkylation of imines derived from chiral aliphatic amines, good yields and moderate to high diastereoselectivity are obtained: yields are significantly better when the preformed imine is used in the reaction with triethyl borane, and diastereoselectivity of the reactions largely depends on the structure of the chiral aliphatic amine. The methodology is successfully applied to the synthesis of romneine, a natural benzylisoquinoline.
The one-pot alkylation of aldimines produces alkylated chiral amines with high yields and diastereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom (X) in the α-position to the starting aldehyde.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36936855</pmid><doi>10.1039/d3ra01397a</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-5149-3576</orcidid><orcidid>https://orcid.org/0000-0003-2422-655X</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Aldehydes Aliphatic amines Alkylation Chemistry Imines Stereoselectivity |
| title | Diastereoselective C-alkylation of aldimines, derived from chiral α-carbon heteroatom-substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines |
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