Diastereo- and Enantioselective Synthesis of Polyfunctional Ketones with Adjacent Quaternary and Tertiary Centers by Asymmetric Carroll Rearrangement
Na . The first asymmetric Carroll rearrangement via dienolate intermediates derived from β‐ketoesters 1 provides access to highly functionalized ketones 2 of high diastereo‐and enantiomeric purity. The chiral auxiliary in this [3,3]sigmatropic rearrangement is (S)‐1‐amino‐2‐methoxymethylpyrrolidine...
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| Veröffentlicht in: | Angewandte Chemie International Edition 1995-11, Vol.34 (20), p.2278-2280 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Enders, Dieter Knopp, Monika Runsink, Jan Raabe, Gerhard |
| description | Na .
The first asymmetric Carroll rearrangement via dienolate intermediates derived from β‐ketoesters 1 provides access to highly functionalized ketones 2 of high diastereo‐and enantiomeric purity. The chiral auxiliary in this [3,3]sigmatropic rearrangement is (S)‐1‐amino‐2‐methoxymethylpyrrolidine (SAMP). The products 2 with adjacent quaternary and tertiary stereogenic centers show promise as versatile building blocks for natural product and drug synthesis. |
| doi_str_mv | 10.1002/anie.199522781 |
| format | Article |
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The first asymmetric Carroll rearrangement via dienolate intermediates derived from β‐ketoesters 1 provides access to highly functionalized ketones 2 of high diastereo‐and enantiomeric purity. The chiral auxiliary in this [3,3]sigmatropic rearrangement is (S)‐1‐amino‐2‐methoxymethylpyrrolidine (SAMP). The products 2 with adjacent quaternary and tertiary stereogenic centers show promise as versatile building blocks for natural product and drug synthesis.</description><identifier>ISSN: 0570-0833</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.199522781</identifier><language>eng</language><publisher>Zug: Hüthig & Wepf Verlag</publisher><subject>asymmetric syntheses ; Carroll rearrangement ; ketones ; SAMP hydrazones</subject><ispartof>Angewandte Chemie International Edition, 1995-11, Vol.34 (20), p.2278-2280</ispartof><rights>Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2421-dc42a1ab87daad5dfb248dbfcd0f69de29ec56eccd166690619e00602b5aade53</citedby><cites>FETCH-LOGICAL-c2421-dc42a1ab87daad5dfb248dbfcd0f69de29ec56eccd166690619e00602b5aade53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.199522781$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.199522781$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Enders, Dieter</creatorcontrib><creatorcontrib>Knopp, Monika</creatorcontrib><creatorcontrib>Runsink, Jan</creatorcontrib><creatorcontrib>Raabe, Gerhard</creatorcontrib><title>Diastereo- and Enantioselective Synthesis of Polyfunctional Ketones with Adjacent Quaternary and Tertiary Centers by Asymmetric Carroll Rearrangement</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed. Engl</addtitle><description>Na .
The first asymmetric Carroll rearrangement via dienolate intermediates derived from β‐ketoesters 1 provides access to highly functionalized ketones 2 of high diastereo‐and enantiomeric purity. The chiral auxiliary in this [3,3]sigmatropic rearrangement is (S)‐1‐amino‐2‐methoxymethylpyrrolidine (SAMP). The products 2 with adjacent quaternary and tertiary stereogenic centers show promise as versatile building blocks for natural product and drug synthesis.</description><subject>asymmetric syntheses</subject><subject>Carroll rearrangement</subject><subject>ketones</subject><subject>SAMP hydrazones</subject><issn>0570-0833</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><recordid>eNqFkMtOwzAQRS0EEuWxZe0fSLGdxkmWVSkFWpVHee0sx56AIXWQbR75EP4XlyLEjtXMaO65mrkIHVDSp4SwQ2kN9GlZZozlBd1APZoxmqR5nm6iHslykpAiTbfRjvdPUV8UhPfQ55GRPoCDNsHSajy20gbTemhABfMGeNHZ8AjeeNzW-KJtuvrVxk1rZYOnEFoLHr-b8IiH-kkqsAFfvspoaKXrvh2vwQWzGkZxCc7jqsND3y2XEJxReCSda5sGX0FspH2AZZTtoa1aNh72f-ouujkeX49Oktn55HQ0nCWKDeJvWg2YpLIqci2lznRdsUGhq1ppUvNSAytBZRyU0pRzXhJOSyCEE1ZlUQ9Zuov6a1_lWu8d1OLFmWU8VlAiVqGKVajiN9QIlGvg3TTQ_aMWw_np-C-brFkTA__4ZaV7FjxP80zczSfi_jafTs6mC7FIvwA5_ZDE</recordid><startdate>19951103</startdate><enddate>19951103</enddate><creator>Enders, Dieter</creator><creator>Knopp, Monika</creator><creator>Runsink, Jan</creator><creator>Raabe, Gerhard</creator><general>Hüthig & Wepf Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19951103</creationdate><title>Diastereo- and Enantioselective Synthesis of Polyfunctional Ketones with Adjacent Quaternary and Tertiary Centers by Asymmetric Carroll Rearrangement</title><author>Enders, Dieter ; Knopp, Monika ; Runsink, Jan ; Raabe, Gerhard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2421-dc42a1ab87daad5dfb248dbfcd0f69de29ec56eccd166690619e00602b5aade53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>asymmetric syntheses</topic><topic>Carroll rearrangement</topic><topic>ketones</topic><topic>SAMP hydrazones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Enders, Dieter</creatorcontrib><creatorcontrib>Knopp, Monika</creatorcontrib><creatorcontrib>Runsink, Jan</creatorcontrib><creatorcontrib>Raabe, Gerhard</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Enders, Dieter</au><au>Knopp, Monika</au><au>Runsink, Jan</au><au>Raabe, Gerhard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereo- and Enantioselective Synthesis of Polyfunctional Ketones with Adjacent Quaternary and Tertiary Centers by Asymmetric Carroll Rearrangement</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed. Engl</addtitle><date>1995-11-03</date><risdate>1995</risdate><volume>34</volume><issue>20</issue><spage>2278</spage><epage>2280</epage><pages>2278-2280</pages><issn>0570-0833</issn><eissn>1521-3773</eissn><abstract>Na .
The first asymmetric Carroll rearrangement via dienolate intermediates derived from β‐ketoesters 1 provides access to highly functionalized ketones 2 of high diastereo‐and enantiomeric purity. The chiral auxiliary in this [3,3]sigmatropic rearrangement is (S)‐1‐amino‐2‐methoxymethylpyrrolidine (SAMP). The products 2 with adjacent quaternary and tertiary stereogenic centers show promise as versatile building blocks for natural product and drug synthesis.</abstract><cop>Zug</cop><pub>Hüthig & Wepf Verlag</pub><doi>10.1002/anie.199522781</doi><tpages>3</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library All Journals |
| subjects | asymmetric syntheses Carroll rearrangement ketones SAMP hydrazones |
| title | Diastereo- and Enantioselective Synthesis of Polyfunctional Ketones with Adjacent Quaternary and Tertiary Centers by Asymmetric Carroll Rearrangement |
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