Enantioselective Brønsted Acid-Catalyzed N-Acyliminium Cyclization Cascades
An enantioselective Brønsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a...
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| Veröffentlicht in: | Journal of the American Chemical Society 2009-08, Vol.131 (31), p.10796-10797 |
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| container_issue | 31 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 131 |
| creator | Muratore, Michael E Holloway, Chloe A Pilling, Adam W Storer, R. Ian Trevitt, Graham Dixon, Darren J |
| description | An enantioselective Brønsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(I)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol % bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63−99%) and high enantioselectivities (72−99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction. |
| doi_str_mv | 10.1021/ja9024885 |
| format | Article |
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With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.</description><subject>Catalysis</subject><subject>Cyclization</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Lactones - chemistry</subject><subject>Organic Chemistry Phenomena</subject><subject>Stereoisomerism</subject><subject>Tryptamines - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1KxDAUhYMozji68AWkGwUX1XuTNk2XYxl_oOhG1yVNUsjQn7Fphc6TuffFjMygG1eXA9_54B5CzhFuECjermUKNBIiPiBzjCmEMVJ-SOYAQMNEcDYjJ86tfYyowGMyw5QDTwHmJF-1sh1s50xt1GA_THDXf322bjA6WCqrw0wOsp62Pj6HSzXVtrGtHZsgm1Rtt9JX2yCTTklt3Ck5qmTtzNn-Lsjb_eo1ewzzl4enbJmHkiEbwrJkMaYRlpFGnvBUSYNCGQYlVKgFCM1iGnHQAqtEKqxEBTRBU2kjEiZStiBXO--m795H44aisU6Zupat6UZXeClNGI89eL0DVd8515uq2PS2kf1UIBQ_0xW_03n2Yi8dy8boP3K_lQcud4BUrlh3Y9_6H_8RfQMpRHUC</recordid><startdate>20090812</startdate><enddate>20090812</enddate><creator>Muratore, Michael E</creator><creator>Holloway, Chloe A</creator><creator>Pilling, Adam W</creator><creator>Storer, R. 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Soc</addtitle><date>2009-08-12</date><risdate>2009</risdate><volume>131</volume><issue>31</issue><spage>10796</spage><epage>10797</epage><pages>10796-10797</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>An enantioselective Brønsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(I)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol % bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63−99%) and high enantioselectivities (72−99% ee). 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| source | ACS Publications; MEDLINE |
| subjects | Catalysis Cyclization Heterocyclic Compounds - chemical synthesis Lactones - chemistry Organic Chemistry Phenomena Stereoisomerism Tryptamines - chemistry |
| title | Enantioselective Brønsted Acid-Catalyzed N-Acyliminium Cyclization Cascades |
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