Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones
[Display omitted] The Ytterbium (III) triflate catalyzed Hantzsch synthesis allows for the preparation of sterically hindered 4-isoxazolyl-1,4-dihydropyridines in moderate to good yields. Asymmetric organocatalysis with (R)-4-Oxo-2,6-bis-(2,4,6-triisopropyl-phenyl)-3,5-dioxa-4l5-phospha-cyclohepta[2...
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| Veröffentlicht in: | Tetrahedron letters 2016-01, Vol.57 (3), p.423-425 |
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| creator | Steiger, Scott A. Li, Chun Campana, Charles F. Natale, Nicholas R. |
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The Ytterbium (III) triflate catalyzed Hantzsch synthesis allows for the preparation of sterically hindered 4-isoxazolyl-1,4-dihydropyridines in moderate to good yields. Asymmetric organocatalysis with (R)-4-Oxo-2,6-bis-(2,4,6-triisopropyl-phenyl)-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a;3,4-a’]dinaphthalen-4-ol (R-TRIP) produces moderate yields of chiral 4-isoxazolyl-quinolones with high enantioselectivity. |
| doi_str_mv | 10.1016/j.tetlet.2015.12.038 |
| format | Article |
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The Ytterbium (III) triflate catalyzed Hantzsch synthesis allows for the preparation of sterically hindered 4-isoxazolyl-1,4-dihydropyridines in moderate to good yields. Asymmetric organocatalysis with (R)-4-Oxo-2,6-bis-(2,4,6-triisopropyl-phenyl)-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a;3,4-a’]dinaphthalen-4-ol (R-TRIP) produces moderate yields of chiral 4-isoxazolyl-quinolones with high enantioselectivity.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2015.12.038</identifier><identifier>PMID: 26783372</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Asymmetric organocatalysis ; chemical reactions ; Dihydropyridine ; enantiomers ; Isoxazole ; Lanthanide catalysis ; organic compounds ; Quinolone ; ytterbium</subject><ispartof>Tetrahedron letters, 2016-01, Vol.57 (3), p.423-425</ispartof><rights>2015 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c566t-17a1e4b37773b70671446bbe5c59c9445578798cc8a69205a6cab91b5737e1b13</citedby><cites>FETCH-LOGICAL-c566t-17a1e4b37773b70671446bbe5c59c9445578798cc8a69205a6cab91b5737e1b13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2015.12.038$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,778,782,883,3539,27911,27912,45982</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26783372$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Steiger, Scott A.</creatorcontrib><creatorcontrib>Li, Chun</creatorcontrib><creatorcontrib>Campana, Charles F.</creatorcontrib><creatorcontrib>Natale, Nicholas R.</creatorcontrib><title>Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones</title><title>Tetrahedron letters</title><addtitle>Tetrahedron Lett</addtitle><description>[Display omitted]
The Ytterbium (III) triflate catalyzed Hantzsch synthesis allows for the preparation of sterically hindered 4-isoxazolyl-1,4-dihydropyridines in moderate to good yields. Asymmetric organocatalysis with (R)-4-Oxo-2,6-bis-(2,4,6-triisopropyl-phenyl)-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a;3,4-a’]dinaphthalen-4-ol (R-TRIP) produces moderate yields of chiral 4-isoxazolyl-quinolones with high enantioselectivity.</description><subject>Asymmetric organocatalysis</subject><subject>chemical reactions</subject><subject>Dihydropyridine</subject><subject>enantiomers</subject><subject>Isoxazole</subject><subject>Lanthanide catalysis</subject><subject>organic compounds</subject><subject>Quinolone</subject><subject>ytterbium</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkTtvFDEUhUcIRJbAP0BoSorMYI-f0yChiJe0Eg3Ulse-y3rlsTe2N8qk5JfHqw2BNODGxfnuuY_TNK8x6jHC_N2uL1A8lH5AmPV46BGRT5oVloJ0hEn8tFkhRFFHERnPmhc571B9XKLnzdnAhSREDKvm11qHstXBWWh1sK3OyzxDSc60Rhftl1uwbV4qAxlyGzdtLlBV7f3Sbl2wkCpAO5fjjb6NfvEdvqCdddvFprhfkrMu1MKj9yPq6uBC9LFqL5tnG-0zvLr_z5sfnz5-v_zSrb99_nr5Yd0ZxnnpsNAY6ESEEGQSiAtMKZ8mYIaNZqSUMSHFKI2Rmo8DYpobPY14YoIIwBMm5837k-_-MM1gDYSStFf75GadFhW1U4-V4LbqZ7xWtLYijFWDt_cGKV4dIBc1u2zAex0gHrIa6n0xHxge_4tiOXDOGJa0ovSEmhRzTrB5mAgjdUxa7dQpaXVMWuFB1aRr2Zu_t3ko-h3tn3Wh3vTaQVLZOAgGrEtgirLR_bvDHQufv08</recordid><startdate>20160120</startdate><enddate>20160120</enddate><creator>Steiger, Scott A.</creator><creator>Li, Chun</creator><creator>Campana, Charles F.</creator><creator>Natale, Nicholas R.</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20160120</creationdate><title>Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones</title><author>Steiger, Scott A. ; Li, Chun ; Campana, Charles F. ; Natale, Nicholas R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c566t-17a1e4b37773b70671446bbe5c59c9445578798cc8a69205a6cab91b5737e1b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Asymmetric organocatalysis</topic><topic>chemical reactions</topic><topic>Dihydropyridine</topic><topic>enantiomers</topic><topic>Isoxazole</topic><topic>Lanthanide catalysis</topic><topic>organic compounds</topic><topic>Quinolone</topic><topic>ytterbium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Steiger, Scott A.</creatorcontrib><creatorcontrib>Li, Chun</creatorcontrib><creatorcontrib>Campana, Charles F.</creatorcontrib><creatorcontrib>Natale, Nicholas R.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Steiger, Scott A.</au><au>Li, Chun</au><au>Campana, Charles F.</au><au>Natale, Nicholas R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones</atitle><jtitle>Tetrahedron letters</jtitle><addtitle>Tetrahedron Lett</addtitle><date>2016-01-20</date><risdate>2016</risdate><volume>57</volume><issue>3</issue><spage>423</spage><epage>425</epage><pages>423-425</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
The Ytterbium (III) triflate catalyzed Hantzsch synthesis allows for the preparation of sterically hindered 4-isoxazolyl-1,4-dihydropyridines in moderate to good yields. Asymmetric organocatalysis with (R)-4-Oxo-2,6-bis-(2,4,6-triisopropyl-phenyl)-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a;3,4-a’]dinaphthalen-4-ol (R-TRIP) produces moderate yields of chiral 4-isoxazolyl-quinolones with high enantioselectivity.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26783372</pmid><doi>10.1016/j.tetlet.2015.12.038</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Tetrahedron letters, 2016-01, Vol.57 (3), p.423-425 |
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| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Asymmetric organocatalysis chemical reactions Dihydropyridine enantiomers Isoxazole Lanthanide catalysis organic compounds Quinolone ytterbium |
| title | Lanthanide and asymmetric catalyzed syntheses of sterically hindered 4-isoxazolyl-1,4-dihydropyridines and 4-isoxazolyl-quinolones |
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