Enantio- and diastereoselective asymmetric allylic alkylation catalyzed by a planar-chiral cyclopentadienyl ruthenium complex
We report asymmetric allylic alkylation of allylic chloride with β-diketones as the prochiral carbon nucleophiles using a planar-chiral Cp'Ru catalyst. The reaction proceeds under mild conditions; the resulting chiral products containing vicinal tertiary stereocenters are obtained with high reg...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2015-07, Vol.51 (54), p.10895-10898 |
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container_title | Chemical communications (Cambridge, England) |
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creator | Kanbayashi, Naoya Hosoda, Kazuki Kato, Masanori Takii, Koichiro Okamura, Taka-aki Onitsuka, Kiyotaka |
description | We report asymmetric allylic alkylation of allylic chloride with β-diketones as the prochiral carbon nucleophiles using a planar-chiral Cp'Ru catalyst. The reaction proceeds under mild conditions; the resulting chiral products containing vicinal tertiary stereocenters are obtained with high regio-, diastereo-, and enantioselectivities. These chiral products can then be transformed into a chiral diol by controlling the four stereocentres. |
doi_str_mv | 10.1039/c5cc02414e |
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These chiral products can then be transformed into a chiral diol by controlling the four stereocentres.</description><subject>Alkylation</subject><subject>Asymmetry</subject><subject>Carbon</subject><subject>Catalysts</subject><subject>Chlorides</subject><subject>Diols</subject><subject>Nucleophiles</subject><subject>Ruthenium</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkUtLxTAQhYMovjf-AMlShGrSJk2zlHJ9gOBGwV2Zm04xmj5MUrGC_93e62PrbM4svjnM4RByxNkZZ5k-N9IYlgoucIPs8iwXiRTF4-ZqlzpRmZA7ZC-EZzYPl8U22UlzJiVTepd8Ljroou0TCl1Nawshosc-oEMT7RtSCFPbYvTWUHBucmt9mRzMRx01EMFNH1jT5USBDg468Il5sh4cNZNx_YBdhNpiNznqx_iEnR1bavp2cPh-QLYacAEPf3SfPFwu7svr5Pbu6qa8uE1MVuQxyZXQSqoGZAPLDFOzZEbOEThTaapkU6TIaqnFSnSha5E2GSLLAWpZmKbI9snJt-_g-9cRQ6xaGwy6-V3sx1BxxbQSXOfyfzTXnHEhCjajp9-o8X0IHptq8LYFP1WcVatmqlKW5bqZxQwf__iOyxbrP_S3iuwLQpOLng</recordid><startdate>20150711</startdate><enddate>20150711</enddate><creator>Kanbayashi, Naoya</creator><creator>Hosoda, Kazuki</creator><creator>Kato, Masanori</creator><creator>Takii, Koichiro</creator><creator>Okamura, Taka-aki</creator><creator>Onitsuka, Kiyotaka</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150711</creationdate><title>Enantio- and diastereoselective asymmetric allylic alkylation catalyzed by a planar-chiral cyclopentadienyl ruthenium complex</title><author>Kanbayashi, Naoya ; Hosoda, Kazuki ; Kato, Masanori ; Takii, Koichiro ; Okamura, Taka-aki ; Onitsuka, Kiyotaka</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c386t-6749757fa5fab3e2cb0c56051072275f82e0d5942e0d989d42f3ee06aad58cf83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkylation</topic><topic>Asymmetry</topic><topic>Carbon</topic><topic>Catalysts</topic><topic>Chlorides</topic><topic>Diols</topic><topic>Nucleophiles</topic><topic>Ruthenium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kanbayashi, Naoya</creatorcontrib><creatorcontrib>Hosoda, Kazuki</creatorcontrib><creatorcontrib>Kato, Masanori</creatorcontrib><creatorcontrib>Takii, Koichiro</creatorcontrib><creatorcontrib>Okamura, Taka-aki</creatorcontrib><creatorcontrib>Onitsuka, Kiyotaka</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kanbayashi, Naoya</au><au>Hosoda, Kazuki</au><au>Kato, Masanori</au><au>Takii, Koichiro</au><au>Okamura, Taka-aki</au><au>Onitsuka, Kiyotaka</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantio- and diastereoselective asymmetric allylic alkylation catalyzed by a planar-chiral cyclopentadienyl ruthenium complex</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2015-07-11</date><risdate>2015</risdate><volume>51</volume><issue>54</issue><spage>10895</spage><epage>10898</epage><pages>10895-10898</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>We report asymmetric allylic alkylation of allylic chloride with β-diketones as the prochiral carbon nucleophiles using a planar-chiral Cp'Ru catalyst. The reaction proceeds under mild conditions; the resulting chiral products containing vicinal tertiary stereocenters are obtained with high regio-, diastereo-, and enantioselectivities. These chiral products can then be transformed into a chiral diol by controlling the four stereocentres.</abstract><cop>England</cop><pmid>26055079</pmid><doi>10.1039/c5cc02414e</doi><tpages>4</tpages></addata></record> |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Alkylation Asymmetry Carbon Catalysts Chlorides Diols Nucleophiles Ruthenium |
title | Enantio- and diastereoselective asymmetric allylic alkylation catalyzed by a planar-chiral cyclopentadienyl ruthenium complex |
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