Enantioselective Reduction of Imines Catalyzed by a Rhenium(V)−Oxo Complex
An air- and moisture-tolerant enantioselective hydrosilylation of N-phosphinyl imines employing a chiral Re(V)−oxo complex as a catalyst is described. The chiral catalyst is a cyanobis(oxazoline) (CNbox)-ligated rhenium−oxo complex of the general formula (CNbox)Re(O)Cl2(OPPh3). Using this catalyst,...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-09, Vol.127 (36), p.12462-12463 |
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| container_end_page | 12463 |
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| container_issue | 36 |
| container_start_page | 12462 |
| container_title | Journal of the American Chemical Society |
| container_volume | 127 |
| creator | Nolin, Kristine A Ahn, Richard W Toste, F. Dean |
| description | An air- and moisture-tolerant enantioselective hydrosilylation of N-phosphinyl imines employing a chiral Re(V)−oxo complex as a catalyst is described. The chiral catalyst is a cyanobis(oxazoline) (CNbox)-ligated rhenium−oxo complex of the general formula (CNbox)Re(O)Cl2(OPPh3). Using this catalyst, a wide range of aromatic imines (including cyclic, acyclic, and heteroaromatic), α-iminoesters, and α,β-unsaturated imines are reduced with good to excellent enantioselectivities. |
| doi_str_mv | 10.1021/ja050831a |
| format | Article |
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Using this catalyst, a wide range of aromatic imines (including cyclic, acyclic, and heteroaromatic), α-iminoesters, and α,β-unsaturated imines are reduced with good to excellent enantioselectivities.</description><subject>Catalysis</subject><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Exact sciences and technology</subject><subject>Imines - chemical synthesis</subject><subject>Imines - chemistry</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Organic chemistry</subject><subject>Organometallic Compounds - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Reactivity and mechanisms</subject><subject>Rhenium - chemistry</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtKw0AUBuBBFK2XhS8g2Si6iM4lmctSijesF7TocjhJTzA1ydRMIq1P4NpH9EmMtNiNqzOH-fg5_ITsMnrMKGcnY6Ax1YLBCumxmNMwZlyukh6llIdKS7FBNr0fd2vENVsnG0yyKBJK9MjgrIKqyZ3HAtMmf8fgAUdt93JV4LLgqswr9EEfGihmHzgKklkAwcMLVnlbHj4dfX9-3U1d0HflpMDpNlnLoPC4s5hbZHh-NuxfhoO7i6v-6SCEKFJNKJmhSZqhlqi5ySQXICCTVIFBnmImYxWbRAsaMQSllZFCKzScgUoYN2KLHMxjJ7V7a9E3tsx9ikUBFbrWW6ljSY3hHTyaw7R23teY2Umdl1DPLKP2tzn711xn9xahbVLiaCkXVXVgfwHAp1BkNVRp7pdOse62SHUunLvcNzj9-4f61UolVGyH94_2Wt3oyDwLe7vMhdTbsWvrqqvunwN_AEGhj_M</recordid><startdate>20050914</startdate><enddate>20050914</enddate><creator>Nolin, Kristine A</creator><creator>Ahn, Richard W</creator><creator>Toste, F. 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Dean</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-6190bcfe86e829f623a3af607a9e2cef65759b83041ea78796387e921a7b1293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Catalysis</topic><topic>Chemical reactivity</topic><topic>Chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Exact sciences and technology</topic><topic>Imines - chemical synthesis</topic><topic>Imines - chemistry</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Organic chemistry</topic><topic>Organometallic Compounds - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Reactivity and mechanisms</topic><topic>Rhenium - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nolin, Kristine A</creatorcontrib><creatorcontrib>Ahn, Richard W</creatorcontrib><creatorcontrib>Toste, F. Dean</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nolin, Kristine A</au><au>Ahn, Richard W</au><au>Toste, F. Dean</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Reduction of Imines Catalyzed by a Rhenium(V)−Oxo Complex</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-09-14</date><risdate>2005</risdate><volume>127</volume><issue>36</issue><spage>12462</spage><epage>12463</epage><pages>12462-12463</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>An air- and moisture-tolerant enantioselective hydrosilylation of N-phosphinyl imines employing a chiral Re(V)−oxo complex as a catalyst is described. The chiral catalyst is a cyanobis(oxazoline) (CNbox)-ligated rhenium−oxo complex of the general formula (CNbox)Re(O)Cl2(OPPh3). Using this catalyst, a wide range of aromatic imines (including cyclic, acyclic, and heteroaromatic), α-iminoesters, and α,β-unsaturated imines are reduced with good to excellent enantioselectivities.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16144373</pmid><doi>10.1021/ja050831a</doi><tpages>2</tpages></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | Catalysis Chemical reactivity Chemistry Crystallography, X-Ray Exact sciences and technology Imines - chemical synthesis Imines - chemistry Models, Molecular Molecular Conformation Organic chemistry Organometallic Compounds - chemistry Oxidation-Reduction Reactivity and mechanisms Rhenium - chemistry Stereoisomerism |
| title | Enantioselective Reduction of Imines Catalyzed by a Rhenium(V)−Oxo Complex |
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