Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched α-Amino Phosphine Oxides
A new method to synthesize chiral α-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or diben...
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| Veröffentlicht in: | Organic letters 2011-04, Vol.13 (8), p.2054-2057 |
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| container_issue | 8 |
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| container_title | Organic letters |
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| creator | Ingle, Gajendrasingh K Liang, Yuxue Mormino, Michael G Li, Guilong Fronczek, Frank R Antilla, Jon C |
| description | A new method to synthesize chiral α-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity. |
| doi_str_mv | 10.1021/ol200456y |
| format | Article |
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The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol200456y</identifier><identifier>PMID: 21413695</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amines - chemistry ; Catalysis ; Imines - chemistry ; Magnesium - chemistry ; Molecular Structure ; Naphthols - chemistry ; Organophosphorus Compounds - chemistry ; Oxides - chemistry ; Phosphines - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2011-04, Vol.13 (8), p.2054-2057</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2011 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a334t-ef803ac2568e7eca671dbcf4219b179c1637fefc92e035ecd147632910199bc3</citedby><cites>FETCH-LOGICAL-a334t-ef803ac2568e7eca671dbcf4219b179c1637fefc92e035ecd147632910199bc3</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/ol200456y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol200456y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21413695$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ingle, Gajendrasingh K</creatorcontrib><creatorcontrib>Liang, Yuxue</creatorcontrib><creatorcontrib>Mormino, Michael G</creatorcontrib><creatorcontrib>Li, Guilong</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Antilla, Jon C</creatorcontrib><title>Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched α-Amino Phosphine Oxides</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A new method to synthesize chiral α-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity.</description><subject>Amines - chemistry</subject><subject>Catalysis</subject><subject>Imines - chemistry</subject><subject>Magnesium - chemistry</subject><subject>Molecular Structure</subject><subject>Naphthols - chemistry</subject><subject>Organophosphorus Compounds - chemistry</subject><subject>Oxides - chemistry</subject><subject>Phosphines - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU1u2zAQhYmiQfPTLnqBgpsiyEItf0TK7CKAYzipAbfuInuCpkYRA4l0RSmJc6tcJGcKCztCC3RFYuZ7b8h5CH2k5AsljH4NDSMkF3L7Bh1RwXhWEMHejndJDtFxjLeE0FRR79AhoznlUokjdD-rXWca_MPceIhuaPHF4udqiX_VIW5q00M2M71pto9Q7mvOm94Fj0OFF61Lom94ai3EiPuA59741AXfOVsnyfNTNk1QGLWAVw-uhPgeHVSmifBhf56g68v59ex7tlxdLWbTZWY4z_sMqgnhxjIhJ1CANbKg5dpWOaNqTQtlqeRFBZVVDAgXYEuaF5IzRQlVam35CTrf2W6GdQulBd-n3-pN51rTbXUwTv_b8a7WN-FO87QqIYpkcLo36MLvAWKvWxctNI3xEIaoJ5IKxblkiTzbkbYLMXZQjVMo0X9i0mNMif3097NG8jWXBHzeAcZGfRuGzqcl_cfoBShrnGg</recordid><startdate>20110415</startdate><enddate>20110415</enddate><creator>Ingle, Gajendrasingh K</creator><creator>Liang, Yuxue</creator><creator>Mormino, Michael G</creator><creator>Li, Guilong</creator><creator>Fronczek, Frank R</creator><creator>Antilla, Jon C</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><scope>5PM</scope></search><sort><creationdate>20110415</creationdate><title>Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched α-Amino Phosphine Oxides</title><author>Ingle, Gajendrasingh K ; Liang, Yuxue ; Mormino, Michael G ; Li, Guilong ; Fronczek, Frank R ; Antilla, Jon C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a334t-ef803ac2568e7eca671dbcf4219b179c1637fefc92e035ecd147632910199bc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Amines - chemistry</topic><topic>Catalysis</topic><topic>Imines - chemistry</topic><topic>Magnesium - chemistry</topic><topic>Molecular Structure</topic><topic>Naphthols - chemistry</topic><topic>Organophosphorus Compounds - chemistry</topic><topic>Oxides - chemistry</topic><topic>Phosphines - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ingle, Gajendrasingh K</creatorcontrib><creatorcontrib>Liang, Yuxue</creatorcontrib><creatorcontrib>Mormino, Michael G</creatorcontrib><creatorcontrib>Li, Guilong</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Antilla, Jon C</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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ingle, Gajendrasingh K</au><au>Liang, Yuxue</au><au>Mormino, Michael G</au><au>Li, Guilong</au><au>Fronczek, Frank R</au><au>Antilla, Jon C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched α-Amino Phosphine Oxides</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2011-04-15</date><risdate>2011</risdate><volume>13</volume><issue>8</issue><spage>2054</spage><epage>2057</epage><pages>2054-2057</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new method to synthesize chiral α-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>21413695</pmid><doi>10.1021/ol200456y</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Organic letters, 2011-04, Vol.13 (8), p.2054-2057 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Amines - chemistry Catalysis Imines - chemistry Magnesium - chemistry Molecular Structure Naphthols - chemistry Organophosphorus Compounds - chemistry Oxides - chemistry Phosphines - chemistry Stereoisomerism |
| title | Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched α-Amino Phosphine Oxides |
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