Highly Stereoselective Synthesis of Substituted γ-Lactams from Acylsilanes
It takes three: The stereoselective synthesis of highly substituted γ‐lactams from amide enolates, acylsilanes, and imines is reported. This multicomponent reaction accesses γ‐amino‐β‐hydroxy amides in a single flask with good yields and excellent levels of diastereoselectivity (see scheme). Exposur...
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| Veröffentlicht in: | Angewandte Chemie (International ed.) 2008-03, Vol.47 (12), p.2294-2297 |
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| container_end_page | 2297 |
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| container_issue | 12 |
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| container_title | Angewandte Chemie (International ed.) |
| container_volume | 47 |
| creator | Lettan, Robert B. II Woodward, Chase C Scheidt, Karl A |
| description | It takes three: The stereoselective synthesis of highly substituted γ‐lactams from amide enolates, acylsilanes, and imines is reported. This multicomponent reaction accesses γ‐amino‐β‐hydroxy amides in a single flask with good yields and excellent levels of diastereoselectivity (see scheme). Exposure of the linear products to microwave irradiation and acidic conditions promotes a cyclization to form the corresponding γ‐lactams in excellent yields. |
| doi_str_mv | 10.1002/anie.200705229 |
| format | Article |
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Exposure of the linear products to microwave irradiation and acidic conditions promotes a cyclization to form the corresponding γ‐lactams in excellent yields.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200705229</identifier><identifier>PMID: 18270992</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH Verlag</publisher><subject>Acylation ; acylsilanes ; Amides - chemistry ; Amination ; chiral auxiliaries ; homoenolates ; Hydroxylation ; Lactams - chemical synthesis ; Lactams - chemistry ; Models, Chemical ; Molecular Structure ; Silanes - chemistry ; Stereoisomerism ; synthetic methods ; γ-lactams</subject><ispartof>Angewandte Chemie (International ed.), 2008-03, Vol.47 (12), p.2294-2297</ispartof><rights>Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. 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Exposure of the linear products to microwave irradiation and acidic conditions promotes a cyclization to form the corresponding γ‐lactams in excellent yields.</description><subject>Acylation</subject><subject>acylsilanes</subject><subject>Amides - chemistry</subject><subject>Amination</subject><subject>chiral auxiliaries</subject><subject>homoenolates</subject><subject>Hydroxylation</subject><subject>Lactams - chemical synthesis</subject><subject>Lactams - chemistry</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Silanes - chemistry</subject><subject>Stereoisomerism</subject><subject>synthetic methods</subject><subject>γ-lactams</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1u1DAUhS0EoqWwZQlZscvgnzi2l6O2TCtGBWlasbQcz3VrSCatrwPkuXgPnomMMirsWN27-M7R0UfIa0YXjFL-3u0iLDilikrOzRNyzCRnpVBKPJ3-SohSacmOyAvErxOvNa2fkyOmuaLG8GPy8SLe3rVjscmQoEdowef4HYrNuMt3gBGLPhSbocEc85BhW_z-Va6dz67DIqS-K5Z-bDG2bgf4kjwLrkV4dbgn5ObD-fXpRbn-tLo8Xa5LX1XSlIwLbWqggVfb2mmpQsN9LZUJmvvgAJjRThhNfWDQOM-CqJtGGSlqvWWgxQl5N_fep_5hAMy2i-ih3Y_oB7SKCiWp3IOLGfSpR0wQ7H2KnUujZdTu9dm9Pvuobwq8OTQPTQfbv_jB1wSYGfgRWxj_U2eXV5fn_5aXczZihp-PWZe-2VpNi-2Xq5Vdn12vuK7O7OeJfzvzwfXW3aaI9mbDKROUakW1EeIP27WVxA</recordid><startdate>20080307</startdate><enddate>20080307</enddate><creator>Lettan, Robert B. 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II</creatorcontrib><creatorcontrib>Woodward, Chase C</creatorcontrib><creatorcontrib>Scheidt, Karl A</creatorcontrib><collection>AGRIS</collection><collection>Istex</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>Angewandte Chemie (International ed.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lettan, Robert B. 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| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie (International ed.), 2008-03, Vol.47 (12), p.2294-2297 |
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| language | eng |
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| source | MEDLINE; Wiley Journals |
| subjects | Acylation acylsilanes Amides - chemistry Amination chiral auxiliaries homoenolates Hydroxylation Lactams - chemical synthesis Lactams - chemistry Models, Chemical Molecular Structure Silanes - chemistry Stereoisomerism synthetic methods γ-lactams |
| title | Highly Stereoselective Synthesis of Substituted γ-Lactams from Acylsilanes |
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