The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as Nucleophiles
The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the...
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| Veröffentlicht in: | Journal of organic chemistry 2003-12, Vol.68 (25), p.9624-9634 |
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| container_end_page | 9634 |
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| container_issue | 25 |
| container_start_page | 9624 |
| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Notz, Wolfgang Tanaka, Fujie Watanabe, Shin-ichi Chowdari, Naidu S Turner, James M Thayumanavan, Rajeswari Barbas, Carlos F |
| description | The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized α- and β-amino acids, β-lactams, and amino alcohols. |
| doi_str_mv | 10.1021/jo0347359 |
| format | Article |
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Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized α- and β-amino acids, β-lactams, and amino alcohols.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0347359</identifier><identifier>PMID: 14656087</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aldehydes - chemistry ; Amino Acids - chemical synthesis ; Amino Acids - chemistry ; Amino Alcohols - chemical synthesis ; Amino Alcohols - chemistry ; Catalysis ; Catalytic reactions ; Chemistry ; Dioxanes ; Exact sciences and technology ; General and physical chemistry ; Imines - chemistry ; Lactams - chemical synthesis ; Lactams - chemistry ; Mannich Bases - chemistry ; Models, Chemical ; Proline - chemistry ; Pyrrolidines - chemistry ; Solvents ; Stereoisomerism ; Structure-Activity Relationship ; Theory of reactions, general kinetics. 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Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Journal of organic chemistry, 2003-12, Vol.68 (25), p.9624-9634</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-365ccab3234a6ba38978a06bf0148a2081a1621c966d2a2d733b18e637bacee03</citedby><cites>FETCH-LOGICAL-a445t-365ccab3234a6ba38978a06bf0148a2081a1621c966d2a2d733b18e637bacee03</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/jo0347359$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0347359$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15350283$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14656087$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Notz, Wolfgang</creatorcontrib><creatorcontrib>Tanaka, Fujie</creatorcontrib><creatorcontrib>Watanabe, Shin-ichi</creatorcontrib><creatorcontrib>Chowdari, Naidu S</creatorcontrib><creatorcontrib>Turner, James M</creatorcontrib><creatorcontrib>Thayumanavan, Rajeswari</creatorcontrib><creatorcontrib>Barbas, Carlos F</creatorcontrib><title>The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as Nucleophiles</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized α- and β-amino acids, β-lactams, and amino alcohols.</description><subject>Aldehydes - chemistry</subject><subject>Amino Acids - chemical synthesis</subject><subject>Amino Acids - chemistry</subject><subject>Amino Alcohols - chemical synthesis</subject><subject>Amino Alcohols - chemistry</subject><subject>Catalysis</subject><subject>Catalytic reactions</subject><subject>Chemistry</subject><subject>Dioxanes</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Imines - chemistry</subject><subject>Lactams - chemical synthesis</subject><subject>Lactams - chemistry</subject><subject>Mannich Bases - chemistry</subject><subject>Models, Chemical</subject><subject>Proline - chemistry</subject><subject>Pyrrolidines - chemistry</subject><subject>Solvents</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Theory of reactions, general kinetics. 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Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Notz, Wolfgang</creatorcontrib><creatorcontrib>Tanaka, Fujie</creatorcontrib><creatorcontrib>Watanabe, Shin-ichi</creatorcontrib><creatorcontrib>Chowdari, Naidu S</creatorcontrib><creatorcontrib>Turner, James M</creatorcontrib><creatorcontrib>Thayumanavan, Rajeswari</creatorcontrib><creatorcontrib>Barbas, Carlos F</creatorcontrib><collection>Istex</collection><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>Notz, Wolfgang</au><au>Tanaka, Fujie</au><au>Watanabe, Shin-ichi</au><au>Chowdari, Naidu S</au><au>Turner, James M</au><au>Thayumanavan, Rajeswari</au><au>Barbas, Carlos F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as Nucleophiles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| ispartof | Journal of organic chemistry, 2003-12, Vol.68 (25), p.9624-9634 |
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| source | MEDLINE; ACS Journals: American Chemical Society Web Editions |
| subjects | Aldehydes - chemistry Amino Acids - chemical synthesis Amino Acids - chemistry Amino Alcohols - chemical synthesis Amino Alcohols - chemistry Catalysis Catalytic reactions Chemistry Dioxanes Exact sciences and technology General and physical chemistry Imines - chemistry Lactams - chemical synthesis Lactams - chemistry Mannich Bases - chemistry Models, Chemical Proline - chemistry Pyrrolidines - chemistry Solvents Stereoisomerism Structure-Activity Relationship Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as Nucleophiles |
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