Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols
A ruthenium‐catalyzed formal anti‐Markovnikov hydroamination of allylic alcohols for the synthesis of chiral γ‐amino alcohols is presented. Proceeding via an asymmetric hydrogen‐borrowing process, the catalysis allows racemic secondary allylic alcohols to react with various amines, affording enantio...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2020-12, Vol.59 (49), p.21959-21964 |
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| creator | Xu, Ruirui Wang, Kun Liu, Haoying Tang, Weijun Sun, Huaming Xue, Dong Xiao, Jianliang Wang, Chao |
| description | A ruthenium‐catalyzed formal anti‐Markovnikov hydroamination of allylic alcohols for the synthesis of chiral γ‐amino alcohols is presented. Proceeding via an asymmetric hydrogen‐borrowing process, the catalysis allows racemic secondary allylic alcohols to react with various amines, affording enantiomerically enriched chiral γ‐amino alcohols with broad substrate scope and excellent enantioselectivities (68 examples, up to >99 % ee).
Anti‐Markovnikov hydroamination of racemic allylic alcohols produces chiral γ‐amino alcohols, which are key intermediates for the synthesis of many drugs and biologically active molecules. Driven by a ruthenium catalyst via a hydrogen borrowing pathway, the reaction features a broad substrate scope (68 examples) and excellent enantioselectivities (up to >99 % ee). |
| doi_str_mv | 10.1002/anie.202009754 |
| format | Article |
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Anti‐Markovnikov hydroamination of racemic allylic alcohols produces chiral γ‐amino alcohols, which are key intermediates for the synthesis of many drugs and biologically active molecules. Driven by a ruthenium catalyst via a hydrogen borrowing pathway, the reaction features a broad substrate scope (68 examples) and excellent enantioselectivities (up to >99 % ee).</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202009754</identifier><identifier>PMID: 32797653</identifier><language>eng</language><publisher>WEINHEIM: Wiley</publisher><subject>Alcohol ; Alcohols ; allylic alcohol ; Amines ; amino alcohol ; asymmetric catalysis ; Catalysis ; Chemistry ; Chemistry, Multidisciplinary ; hydrogen borrowing ; Physical Sciences ; Ruthenium ; ruthenium catalyst ; Science & Technology ; Substrates</subject><ispartof>Angewandte Chemie International Edition, 2020-12, Vol.59 (49), p.21959-21964</ispartof><rights>2020 Wiley‐VCH GmbH</rights><rights>2020 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>49</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000573540200001</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c3734-32b1e68150d0fb1d896289715c8448164969232b157d423933da8a0859c092063</citedby><cites>FETCH-LOGICAL-c3734-32b1e68150d0fb1d896289715c8448164969232b157d423933da8a0859c092063</cites><orcidid>0000-0003-4812-6000</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.202009754$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202009754$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27928,27929,28252,45578,45579</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32797653$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xu, Ruirui</creatorcontrib><creatorcontrib>Wang, Kun</creatorcontrib><creatorcontrib>Liu, Haoying</creatorcontrib><creatorcontrib>Tang, Weijun</creatorcontrib><creatorcontrib>Sun, Huaming</creatorcontrib><creatorcontrib>Xue, Dong</creatorcontrib><creatorcontrib>Xiao, Jianliang</creatorcontrib><creatorcontrib>Wang, Chao</creatorcontrib><title>Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols</title><title>Angewandte Chemie International Edition</title><addtitle>ANGEW CHEM INT EDIT</addtitle><addtitle>Angew Chem Int Ed Engl</addtitle><description>A ruthenium‐catalyzed formal anti‐Markovnikov hydroamination of allylic alcohols for the synthesis of chiral γ‐amino alcohols is presented. Proceeding via an asymmetric hydrogen‐borrowing process, the catalysis allows racemic secondary allylic alcohols to react with various amines, affording enantiomerically enriched chiral γ‐amino alcohols with broad substrate scope and excellent enantioselectivities (68 examples, up to >99 % ee).
Anti‐Markovnikov hydroamination of racemic allylic alcohols produces chiral γ‐amino alcohols, which are key intermediates for the synthesis of many drugs and biologically active molecules. Driven by a ruthenium catalyst via a hydrogen borrowing pathway, the reaction features a broad substrate scope (68 examples) and excellent enantioselectivities (up to >99 % ee).</description><subject>Alcohol</subject><subject>Alcohols</subject><subject>allylic alcohol</subject><subject>Amines</subject><subject>amino alcohol</subject><subject>asymmetric catalysis</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry, Multidisciplinary</subject><subject>hydrogen borrowing</subject><subject>Physical Sciences</subject><subject>Ruthenium</subject><subject>ruthenium catalyst</subject><subject>Science & Technology</subject><subject>Substrates</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>AOWDO</sourceid><recordid>eNqN0U1u1DAUB_AIUdFS2LJEkdhUQhme7fhrGUUtrVSKhGAdOY6jujh2sRPQ7HqE3oV7cAhOgqczDBIb2Nhe_N7fz89F8QLBCgHgN8pbs8KAASSn9aPiCFGMKsI5eZzPNSEVFxQdFk9TusleCGBPikOCueSMkqOib_xsf97dv1Pxc_jqbV7K8_UQg5qsV7MNvgxj-UFpM1ldNs6t3cOuw3VwqZxD2WhtUirbaxuVK398z2FNrg179Kw4GJVL5vluPy4-nZ1-bM-ry_dvL9rmstKEk7oiuEeGCURhgLFHg5AMC8kR1aKuBWK1ZBJvEOVDjYkkZFBCgaBSg8TAyHFxss29jeHLYtLcTTZp45zyJiypwzXJQZgAzvTVX_QmLNHn7rJihLF8HWS12iodQ0rRjN1ttJOK6w5Bt5l-t5l-t59-Lni5i136yQx7_nvcGbzegm-mD2PS1nht9gwAKCe03uQBoKzF_-vWzg_f1YbFz7lU7kqtM-t_9N01Vxenf17xC3p_sYY</recordid><startdate>20201201</startdate><enddate>20201201</enddate><creator>Xu, Ruirui</creator><creator>Wang, Kun</creator><creator>Liu, Haoying</creator><creator>Tang, Weijun</creator><creator>Sun, Huaming</creator><creator>Xue, Dong</creator><creator>Xiao, Jianliang</creator><creator>Wang, Chao</creator><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>1KM</scope><scope>1KN</scope><scope>AOWDO</scope><scope>BLEPL</scope><scope>DTL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4812-6000</orcidid></search><sort><creationdate>20201201</creationdate><title>Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols</title><author>Xu, Ruirui ; Wang, Kun ; Liu, Haoying ; Tang, Weijun ; Sun, Huaming ; Xue, Dong ; Xiao, Jianliang ; Wang, Chao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3734-32b1e68150d0fb1d896289715c8448164969232b157d423933da8a0859c092063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alcohol</topic><topic>Alcohols</topic><topic>allylic alcohol</topic><topic>Amines</topic><topic>amino alcohol</topic><topic>asymmetric catalysis</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemistry, Multidisciplinary</topic><topic>hydrogen borrowing</topic><topic>Physical Sciences</topic><topic>Ruthenium</topic><topic>ruthenium catalyst</topic><topic>Science & Technology</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xu, Ruirui</creatorcontrib><creatorcontrib>Wang, Kun</creatorcontrib><creatorcontrib>Liu, Haoying</creatorcontrib><creatorcontrib>Tang, Weijun</creatorcontrib><creatorcontrib>Sun, Huaming</creatorcontrib><creatorcontrib>Xue, Dong</creatorcontrib><creatorcontrib>Xiao, Jianliang</creatorcontrib><creatorcontrib>Wang, Chao</creatorcontrib><collection>Index Chemicus</collection><collection>Current Chemical Reactions</collection><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xu, Ruirui</au><au>Wang, Kun</au><au>Liu, Haoying</au><au>Tang, Weijun</au><au>Sun, Huaming</au><au>Xue, Dong</au><au>Xiao, Jianliang</au><au>Wang, Chao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols</atitle><jtitle>Angewandte Chemie International Edition</jtitle><stitle>ANGEW CHEM INT EDIT</stitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2020-12-01</date><risdate>2020</risdate><volume>59</volume><issue>49</issue><spage>21959</spage><epage>21964</epage><pages>21959-21964</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A ruthenium‐catalyzed formal anti‐Markovnikov hydroamination of allylic alcohols for the synthesis of chiral γ‐amino alcohols is presented. Proceeding via an asymmetric hydrogen‐borrowing process, the catalysis allows racemic secondary allylic alcohols to react with various amines, affording enantiomerically enriched chiral γ‐amino alcohols with broad substrate scope and excellent enantioselectivities (68 examples, up to >99 % ee).
Anti‐Markovnikov hydroamination of racemic allylic alcohols produces chiral γ‐amino alcohols, which are key intermediates for the synthesis of many drugs and biologically active molecules. Driven by a ruthenium catalyst via a hydrogen borrowing pathway, the reaction features a broad substrate scope (68 examples) and excellent enantioselectivities (up to >99 % ee).</abstract><cop>WEINHEIM</cop><pub>Wiley</pub><pmid>32797653</pmid><doi>10.1002/anie.202009754</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-4812-6000</orcidid></addata></record> |
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| subjects | Alcohol Alcohols allylic alcohol Amines amino alcohol asymmetric catalysis Catalysis Chemistry Chemistry, Multidisciplinary hydrogen borrowing Physical Sciences Ruthenium ruthenium catalyst Science & Technology Substrates |
| title | Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols |
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