Central-to-axial chirality induction in biphenyl chiroptical probes for the stereochemical characterization of chiral primary amines
Flexible biphenyls have been applied as efficient and practical chiroptical probes for absolute configuration assignment to chiral primary amines. The mechanism of the central-to-axial chirality transfer from the amine moiety to the conformationally flexible biphenyl system has been determined by NM...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2018, Vol.16 (4), p.555-565 |
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| creator | Vergura, S Pisani, L Scafato, P Casarini, D Superchi, S |
| description | Flexible biphenyls have been applied as efficient and practical chiroptical probes for absolute configuration assignment to chiral primary amines. The mechanism of the central-to-axial chirality transfer from the amine moiety to the conformationally flexible biphenyl system has been determined by NMR and computational studies. This allowed proposing a general non-empirical rule in order to establish, simply by looking at the sign of the 250 nm A band in the ECD spectrum of the biphenyl derivative, the torsion of the biphenyl and thus the absolute configuration of the amine. The method proved to be very reliable and sensitive, allowing treatment of samples on the μmol scale and permitting the simultaneous determination of the amine sample's absolute configuration and enantiopurity. |
| doi_str_mv | 10.1039/c7ob02730c |
| format | Article |
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The mechanism of the central-to-axial chirality transfer from the amine moiety to the conformationally flexible biphenyl system has been determined by NMR and computational studies. This allowed proposing a general non-empirical rule in order to establish, simply by looking at the sign of the 250 nm A band in the ECD spectrum of the biphenyl derivative, the torsion of the biphenyl and thus the absolute configuration of the amine. 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The mechanism of the central-to-axial chirality transfer from the amine moiety to the conformationally flexible biphenyl system has been determined by NMR and computational studies. This allowed proposing a general non-empirical rule in order to establish, simply by looking at the sign of the 250 nm A band in the ECD spectrum of the biphenyl derivative, the torsion of the biphenyl and thus the absolute configuration of the amine. The method proved to be very reliable and sensitive, allowing treatment of samples on the μmol scale and permitting the simultaneous determination of the amine sample's absolute configuration and enantiopurity.</description><subject>Absolute configuration</subject><subject>Amines</subject><subject>Biphenyl</subject><subject>Chirality</subject><subject>Computer applications</subject><subject>Configurations</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Probes</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkU1LxDAQhoMouq5e_AFS8CJCNWnaJnPU4hcseNFzSdOERtpmTVJwPfvDjbvrHmQOM5N58jLDi9AZwdcEU7iRzDY4YxTLPTQjOWMpLijs7-oMH6Fj798xJsDK_BAdZRAjz7MZ-q7UGJzo02BT8WlEn8jOxN6EVWLGdpLB2DFWSWOWnRpXm7ldBiMju3S2UT7R1iWhU4kPyikrOzWsp7ITTsj4Zr7EWsbqrXr8aAbhVokYzKj8CTrQovfqdJvn6O3h_rV6Shcvj8_V7SKVlJOQCok54QVoCg3kJbRtpuM9RQFAGpaxRuiCc8xxC4yVUICimqqSQiaklrGbo8uNbtz7Y1I-1IPxUvW9GJWdfE2AU17kmPOIXvxD3-3kxrhdnWGCOQMof6mrDSWd9d4pXW8Pqwmuf72pK_Zyt_amivD5VnJqBtXu0D8z6A_3v4uF</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Vergura, S</creator><creator>Pisani, L</creator><creator>Scafato, P</creator><creator>Casarini, D</creator><creator>Superchi, S</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4101-8541</orcidid><orcidid>https://orcid.org/0000-0002-6301-2856</orcidid><orcidid>https://orcid.org/0000-0002-7265-1625</orcidid><orcidid>https://orcid.org/0000-0001-6325-2027</orcidid></search><sort><creationdate>2018</creationdate><title>Central-to-axial chirality induction in biphenyl chiroptical probes for the stereochemical characterization of chiral primary amines</title><author>Vergura, S ; Pisani, L ; Scafato, P ; Casarini, D ; Superchi, S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-ac081859f39b9469dd2f76455991b727baf588080d9776959e3f3e6392acfc9e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Absolute configuration</topic><topic>Amines</topic><topic>Biphenyl</topic><topic>Chirality</topic><topic>Computer applications</topic><topic>Configurations</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Probes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vergura, S</creatorcontrib><creatorcontrib>Pisani, L</creatorcontrib><creatorcontrib>Scafato, P</creatorcontrib><creatorcontrib>Casarini, D</creatorcontrib><creatorcontrib>Superchi, S</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vergura, S</au><au>Pisani, L</au><au>Scafato, P</au><au>Casarini, D</au><au>Superchi, S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Central-to-axial chirality induction in biphenyl chiroptical probes for the stereochemical characterization of chiral primary amines</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2018</date><risdate>2018</risdate><volume>16</volume><issue>4</issue><spage>555</spage><epage>565</epage><pages>555-565</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Flexible biphenyls have been applied as efficient and practical chiroptical probes for absolute configuration assignment to chiral primary amines. 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| ispartof | Organic & biomolecular chemistry, 2018, Vol.16 (4), p.555-565 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Absolute configuration Amines Biphenyl Chirality Computer applications Configurations NMR Nuclear magnetic resonance Probes |
| title | Central-to-axial chirality induction in biphenyl chiroptical probes for the stereochemical characterization of chiral primary amines |
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