Stereoselective Formation of N-Acyliminium Ion via Chiral N,O-Acetal TMS Ether and Its Application to the Synthesis of β-Amino Acids
The highly stereoselective synthesis of β-amino acids via the chiral 4-phenyloxazolidinone-controlled linear N-acyliminium ion reaction has been achieved by employing chiral N,O-acetal TMS ethers. In addition, the mechanism of the excellent stereochemical outcome has been elucidated. The oxazolidino...
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| Veröffentlicht in: | Organic letters 2003-10, Vol.5 (20), p.3635-3638 |
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| container_title | Organic letters |
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| creator | Shin, Dong-Yun Jung, Jae-Kyung Seo, Seung-Yong Lee, Yong-Sil Paek, Seung-Mann Chung, Young Keun Shin, Dong Mok Suh, Young-Ger |
| description | The highly stereoselective synthesis of β-amino acids via the chiral 4-phenyloxazolidinone-controlled linear N-acyliminium ion reaction has been achieved by employing chiral N,O-acetal TMS ethers. In addition, the mechanism of the excellent stereochemical outcome has been elucidated. The oxazolidinone auxiliary plays a dual role in stereocontrol: the E/Z geometry control of the N-acyliminium ion induced by an initial stereoselective amide reduction, leading to the chiral N,O-acetal TMS ether, and face control of the nucleophile attack in the N-acyliminium ion reaction. |
| doi_str_mv | 10.1021/ol035289e |
| format | Article |
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The oxazolidinone auxiliary plays a dual role in stereocontrol: the E/Z geometry control of the N-acyliminium ion induced by an initial stereoselective amide reduction, leading to the chiral N,O-acetal TMS ether, and face control of the nucleophile attack in the N-acyliminium ion reaction.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol035289e</identifier><identifier>PMID: 14507191</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Acetals - chemistry ; Acylation ; Amino Acids - chemical synthesis ; Cations - chemistry ; Crystallography, X-Ray ; Ethers - chemistry ; Imines - chemistry ; Molecular Structure ; Oxazolidinones - chemistry ; Stereoisomerism ; Trimethylsilyl Compounds - chemistry</subject><ispartof>Organic letters, 2003-10, Vol.5 (20), p.3635-3638</ispartof><rights>Copyright © 2003 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a311t-12a06b764f72b3b011363e675356af60603121dd48be5a5a13696e849b06d3673</citedby><cites>FETCH-LOGICAL-a311t-12a06b764f72b3b011363e675356af60603121dd48be5a5a13696e849b06d3673</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/ol035289e$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol035289e$$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/14507191$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shin, Dong-Yun</creatorcontrib><creatorcontrib>Jung, Jae-Kyung</creatorcontrib><creatorcontrib>Seo, Seung-Yong</creatorcontrib><creatorcontrib>Lee, Yong-Sil</creatorcontrib><creatorcontrib>Paek, Seung-Mann</creatorcontrib><creatorcontrib>Chung, Young Keun</creatorcontrib><creatorcontrib>Shin, Dong Mok</creatorcontrib><creatorcontrib>Suh, Young-Ger</creatorcontrib><title>Stereoselective Formation of N-Acyliminium Ion via Chiral N,O-Acetal TMS Ether and Its Application to the Synthesis of β-Amino Acids</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The highly stereoselective synthesis of β-amino acids via the chiral 4-phenyloxazolidinone-controlled linear N-acyliminium ion reaction has been achieved by employing chiral N,O-acetal TMS ethers. In addition, the mechanism of the excellent stereochemical outcome has been elucidated. The oxazolidinone auxiliary plays a dual role in stereocontrol: the E/Z geometry control of the N-acyliminium ion induced by an initial stereoselective amide reduction, leading to the chiral N,O-acetal TMS ether, and face control of the nucleophile attack in the N-acyliminium ion reaction.</description><subject>Acetals - chemistry</subject><subject>Acylation</subject><subject>Amino Acids - chemical synthesis</subject><subject>Cations - chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Ethers - chemistry</subject><subject>Imines - chemistry</subject><subject>Molecular Structure</subject><subject>Oxazolidinones - chemistry</subject><subject>Stereoisomerism</subject><subject>Trimethylsilyl Compounds - chemistry</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>eNptkN9KwzAUh4Mo_r_wBSQ3CoLVpGnS9rKMqYO5XWxel7Q9ZRltU5N0sAfwhXwQn8nIht54dQ7n9_HB-SF0RckDJSF91A1hPExSOECnlIcsiAkPD393QU7QmbVrQqi_pMfohEacxDSlp-hj4cCAttBA6dQG8JM2rXRKd1jXeBZk5bZRrerU0OKJP26UxKOVMrLBs_u5j8H5dfm6wGO3AoNlV-GJszjr-0aVO5HT2Gd4se38sMr-mL8-g8xrNc5KVdkLdFTLxsLlfp6jt6fxcvQSTOfPk1E2DSSj1AU0lEQUsYjqOCxY4d9hgoGIOeNC1sI_ymhIqypKCuCSSx-nApIoLYiomIjZObrdeXuj3wewLm-VLaFpZAd6sHnMYxJxnnjwbgeWRltroM57o1pptjkl-U_n-W_nnr3eS4eiheqP3JfsgZsdIEubr_VgOv_jP6Jv95WHWA</recordid><startdate>20031002</startdate><enddate>20031002</enddate><creator>Shin, Dong-Yun</creator><creator>Jung, Jae-Kyung</creator><creator>Seo, Seung-Yong</creator><creator>Lee, Yong-Sil</creator><creator>Paek, Seung-Mann</creator><creator>Chung, Young Keun</creator><creator>Shin, Dong Mok</creator><creator>Suh, Young-Ger</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20031002</creationdate><title>Stereoselective Formation of N-Acyliminium Ion via Chiral N,O-Acetal TMS Ether and Its Application to the Synthesis of β-Amino Acids</title><author>Shin, Dong-Yun ; Jung, Jae-Kyung ; Seo, Seung-Yong ; Lee, Yong-Sil ; Paek, Seung-Mann ; Chung, Young Keun ; Shin, Dong Mok ; Suh, Young-Ger</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-12a06b764f72b3b011363e675356af60603121dd48be5a5a13696e849b06d3673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Acetals - chemistry</topic><topic>Acylation</topic><topic>Amino Acids - chemical synthesis</topic><topic>Cations - chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Ethers - chemistry</topic><topic>Imines - chemistry</topic><topic>Molecular Structure</topic><topic>Oxazolidinones - chemistry</topic><topic>Stereoisomerism</topic><topic>Trimethylsilyl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shin, Dong-Yun</creatorcontrib><creatorcontrib>Jung, Jae-Kyung</creatorcontrib><creatorcontrib>Seo, Seung-Yong</creatorcontrib><creatorcontrib>Lee, Yong-Sil</creatorcontrib><creatorcontrib>Paek, Seung-Mann</creatorcontrib><creatorcontrib>Chung, Young Keun</creatorcontrib><creatorcontrib>Shin, Dong Mok</creatorcontrib><creatorcontrib>Suh, Young-Ger</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>Shin, Dong-Yun</au><au>Jung, Jae-Kyung</au><au>Seo, Seung-Yong</au><au>Lee, Yong-Sil</au><au>Paek, Seung-Mann</au><au>Chung, Young Keun</au><au>Shin, Dong Mok</au><au>Suh, Young-Ger</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereoselective Formation of N-Acyliminium Ion via Chiral N,O-Acetal TMS Ether and Its Application to the Synthesis of β-Amino Acids</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2003-10-02</date><risdate>2003</risdate><volume>5</volume><issue>20</issue><spage>3635</spage><epage>3638</epage><pages>3635-3638</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The highly stereoselective synthesis of β-amino acids via the chiral 4-phenyloxazolidinone-controlled linear N-acyliminium ion reaction has been achieved by employing chiral N,O-acetal TMS ethers. In addition, the mechanism of the excellent stereochemical outcome has been elucidated. The oxazolidinone auxiliary plays a dual role in stereocontrol: the E/Z geometry control of the N-acyliminium ion induced by an initial stereoselective amide reduction, leading to the chiral N,O-acetal TMS ether, and face control of the nucleophile attack in the N-acyliminium ion reaction.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>14507191</pmid><doi>10.1021/ol035289e</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2003-10, Vol.5 (20), p.3635-3638 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Acetals - chemistry Acylation Amino Acids - chemical synthesis Cations - chemistry Crystallography, X-Ray Ethers - chemistry Imines - chemistry Molecular Structure Oxazolidinones - chemistry Stereoisomerism Trimethylsilyl Compounds - chemistry |
| title | Stereoselective Formation of N-Acyliminium Ion via Chiral N,O-Acetal TMS Ether and Its Application to the Synthesis of β-Amino Acids |
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