Organocatalytic Asymmetric Assembly Reactions: One-Pot Synthesis of Functionalized β-Amino Alcohols from Aldehydes, Ketones, and Azodicarboxylates
l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active β-amino alcohols. This assembly reaction uses both aldehydes and ketones as donors in one pot. The aldol-derived stereocenter is formed with a reduced fac...
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| Veröffentlicht in: | Organic letters 2003-05, Vol.5 (10), p.1685-1688 |
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| container_title | Organic letters |
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| creator | Chowdari, Naidu S Ramachary, D. B Barbas, Carlos F |
| description | l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active β-amino alcohols. This assembly reaction uses both aldehydes and ketones as donors in one pot. The aldol-derived stereocenter is formed with a reduced facial selectivity in reactions involving (R)-amino aldehydes. The reactions can be performed on a multigram scale under operationally simple and safe conditions without the requirement of an inert atmosphere or dry solvents. |
| doi_str_mv | 10.1021/ol034333n |
| format | Article |
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The reactions can be performed on a multigram scale under operationally simple and safe conditions without the requirement of an inert atmosphere or dry solvents.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol034333n</identifier><identifier>PMID: 12735752</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Aldehydes - chemistry ; Amino Alcohols - chemical synthesis ; Aza Compounds - chemical synthesis ; Aza Compounds - chemistry ; Catalysis ; Dicarboxylic Acids - chemical synthesis ; Dicarboxylic Acids - chemistry ; Ketones - chemistry ; Models, Molecular ; Molecular Conformation ; Proline - chemistry ; Solvents ; Stereoisomerism</subject><ispartof>Organic letters, 2003-05, Vol.5 (10), p.1685-1688</ispartof><rights>Copyright © 2003 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a311t-c287496be6242d35fc46598bfdb897a3d723c0a1bffa1929865d571f2646c3f83</citedby><cites>FETCH-LOGICAL-a311t-c287496be6242d35fc46598bfdb897a3d723c0a1bffa1929865d571f2646c3f83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol034333n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol034333n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12735752$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chowdari, Naidu S</creatorcontrib><creatorcontrib>Ramachary, D. B</creatorcontrib><creatorcontrib>Barbas, Carlos F</creatorcontrib><title>Organocatalytic Asymmetric Assembly Reactions: One-Pot Synthesis of Functionalized β-Amino Alcohols from Aldehydes, Ketones, and Azodicarboxylates</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active β-amino alcohols. This assembly reaction uses both aldehydes and ketones as donors in one pot. The aldol-derived stereocenter is formed with a reduced facial selectivity in reactions involving (R)-amino aldehydes. The reactions can be performed on a multigram scale under operationally simple and safe conditions without the requirement of an inert atmosphere or dry solvents.</description><subject>Aldehydes - chemistry</subject><subject>Amino Alcohols - chemical synthesis</subject><subject>Aza Compounds - chemical synthesis</subject><subject>Aza Compounds - chemistry</subject><subject>Catalysis</subject><subject>Dicarboxylic Acids - chemical synthesis</subject><subject>Dicarboxylic Acids - chemistry</subject><subject>Ketones - chemistry</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Proline - chemistry</subject><subject>Solvents</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU1u1TAUhS3Uiv7QARtAnoCERIp_8sssqiigVnoI6Dhy7GteKscuvo5EOuqUDbAQFsIiWAlp31M76eiee_TpDM4h5Dlnx5wJ_jY4JnMppX9C9nkhZFaxQuzc65LtkQPES8b44jRPyR4XlSyqQuyT36v4XfmgVVJuToOmLc7jCCneSYSxdzP9AkqnIXh89-_mF115yD6HRL_OPq0BB6TB0tPJ3yHKDddg6N8_WTsOPtDW6bAODqmNYVw-A-vZAL6hZ5CCvxXKG9peBzNoFfvwc3YqAT4ju1Y5hKPtPSQXp--_nXzMzlcfPp2055mSnKdMi7rKm7KHUuTCyMLqvCyauremr5tKSVMJqZnivbWKN6Kpy8IUFbeizEstbS0PyatN7lUMPybA1I0DanBOeQgTdpUUS3-1WMDXG1DHgBjBdldxGFWcO8662xG6-xEW9sU2dOpHMA_ktvUFeLkBlMbuMkxxqQ0fCfoP_7SSAQ</recordid><startdate>20030515</startdate><enddate>20030515</enddate><creator>Chowdari, Naidu S</creator><creator>Ramachary, D. 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B ; Barbas, Carlos F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-c287496be6242d35fc46598bfdb897a3d723c0a1bffa1929865d571f2646c3f83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Aldehydes - chemistry</topic><topic>Amino Alcohols - chemical synthesis</topic><topic>Aza Compounds - chemical synthesis</topic><topic>Aza Compounds - chemistry</topic><topic>Catalysis</topic><topic>Dicarboxylic Acids - chemical synthesis</topic><topic>Dicarboxylic Acids - chemistry</topic><topic>Ketones - chemistry</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Proline - chemistry</topic><topic>Solvents</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chowdari, Naidu S</creatorcontrib><creatorcontrib>Ramachary, D. B</creatorcontrib><creatorcontrib>Barbas, Carlos F</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chowdari, Naidu S</au><au>Ramachary, D. B</au><au>Barbas, Carlos F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organocatalytic Asymmetric Assembly Reactions: One-Pot Synthesis of Functionalized β-Amino Alcohols from Aldehydes, Ketones, and Azodicarboxylates</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2003-05-15</date><risdate>2003</risdate><volume>5</volume><issue>10</issue><spage>1685</spage><epage>1688</epage><pages>1685-1688</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active β-amino alcohols. This assembly reaction uses both aldehydes and ketones as donors in one pot. The aldol-derived stereocenter is formed with a reduced facial selectivity in reactions involving (R)-amino aldehydes. The reactions can be performed on a multigram scale under operationally simple and safe conditions without the requirement of an inert atmosphere or dry solvents.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>12735752</pmid><doi>10.1021/ol034333n</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2003-05, Vol.5 (10), p.1685-1688 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Aldehydes - chemistry Amino Alcohols - chemical synthesis Aza Compounds - chemical synthesis Aza Compounds - chemistry Catalysis Dicarboxylic Acids - chemical synthesis Dicarboxylic Acids - chemistry Ketones - chemistry Models, Molecular Molecular Conformation Proline - chemistry Solvents Stereoisomerism |
| title | Organocatalytic Asymmetric Assembly Reactions: One-Pot Synthesis of Functionalized β-Amino Alcohols from Aldehydes, Ketones, and Azodicarboxylates |
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