FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2040079916> ?p ?o ?g. }

• W2040079916 endingPage "3654" @default.
• W2040079916 startingPage "3643" @default.
• W2040079916 abstract "ConspectusAmplification of enantiomeric excess (ee) is a key feature for the chemical evolution of biological homochirality from the origin of chirality. We describe the amplification of ee in the asymmetric autocatalysis of 5-pyrimidyl alkanols in the reaction between diisopropylzinc (i-Pr2Zn) and pyrimidine-5-carbaldehydes. During the reaction, an extremely low ee (ca. 0.00005% ee) can be amplified to >99.5% ee, and therefore, the initial slightly major enantiomer is automultiplied by a factor of ca. 630000, while the initial slightly minor enantiomer is automultiplied by a factor of less than 1000. In addition, pyrimidyl alkanols with various substituents at the 2-position of the pyrimidine ring, 3-quinolyl alkanol, 5-carbamoyl-3-pyridyl alkanol, and large multifunctionalized pyrimidyl alkanols also act as highly efficient asymmetric autocatalysts in the addition of i-Pr2Zn to the corresponding aldehydes.The asymmetric autocatalysis of pyrimidyl alkanol can discriminate the chirality of various compounds. Chiral substances such as alcohols, amino acids, hydrocarbons, metal complexes, and heterogeneous chiral materials can act as chiral triggers for asymmetric autocatalysis to afford pyrimidyl alkanols with the corresponding absolute configuration of the initiator. This recognition ability of chiral compounds is extremely high, and chiral discrimination of a cryptochiral quaternary saturated hydrocarbon was established by applying asymmetric autocatalysis.By using the large amplification effect of the asymmetric autocatalysis, we can link various proposed origins of chirality with highly enantioenriched organic compounds in conjunction with asymmetric autocatalysis. Thus, a statistical fluctuation in ee of racemic compounds can be amplified to high ee by using asymmetric autocatalysis. Enantiomeric imbalance induced by irradiation of circularly polarized light can affect the enantioselectivity of asymmetric autocatalysis. The asymmetric autocatalysis was also triggered by the morphology of inorganic chiral crystals such as quartz, sodium chlorate, and cinnabar. Chiral organic crystals of achiral compounds also act as chiral initiators, and during the study of a crystal of cytosine, enantioselective chiral crystal phase transformation of the cytosine crystal was achieved by removal of the water of crystallization in an achiral monohydrate crystal. Enantioselective C–C bond formation was realized on the surfaces of achiral single crystals based on the oriented prochirality of achiral aldehydes. Furthermore, asymmetric autocatalysis of pyrimidyl alkanols is a highly sensitive reaction that can recognize and amplify the significantly small effect of a chiral compound arising solely from isotope substitution of hydrogen, carbon, and oxygen (D/H, 13C/12C, and 18O/16O). These examples show that asymmetric autocatalysis with an amplification of chirality is a powerful tool for correlating the origin of chirality with highly enantioenriched organic compounds.Asymmetric autocatalysis using two β-amino alcohols reveals a reversal of enantioselectivity in the addition of i-Pr2Zn to aldehyde and is one approach toward understanding the mechanism of asymmetric dialkylzinc addition, where heteroaggregates act as the catalytic species." @default.
• W2040079916 created "2016-06-24" @default.
• W2040079916 creator A5038165443 @default.
• W2040079916 creator A5057345662 @default.
• W2040079916 creator A5058976206 @default.
• W2040079916 date "2014-11-19" @default.
• W2040079916 modified "2023-10-18" @default.
• W2040079916 title "Asymmetric Autocatalysis of Pyrimidyl Alkanol and Its Application to the Study on the Origin of Homochirality" @default.
• W2040079916 cites W1519666880 @default.
• W2040079916 cites W1830333769 @default.
• W2040079916 cites W1964466175 @default.
• W2040079916 cites W1971418244 @default.
• W2040079916 cites W1971881482 @default.
• W2040079916 cites W1979476032 @default.
• W2040079916 cites W1979583065 @default.
• W2040079916 cites W1985118658 @default.
• W2040079916 cites W1985513031 @default.
• W2040079916 cites W1987032187 @default.
• W2040079916 cites W1987406969 @default.
• W2040079916 cites W1990419655 @default.
• W2040079916 cites W1999909978 @default.
• W2040079916 cites W2000236822 @default.
• W2040079916 cites W2000713249 @default.
• W2040079916 cites W2002050731 @default.
• W2040079916 cites W2007151621 @default.
• W2040079916 cites W2009930537 @default.
• W2040079916 cites W2010197431 @default.
• W2040079916 cites W2012589375 @default.
• W2040079916 cites W2016267837 @default.
• W2040079916 cites W2020333913 @default.
• W2040079916 cites W2026655238 @default.
• W2040079916 cites W2027027985 @default.
• W2040079916 cites W2029164996 @default.
• W2040079916 cites W2032638412 @default.
• W2040079916 cites W2036886809 @default.
• W2040079916 cites W2037124632 @default.
• W2040079916 cites W2046245747 @default.
• W2040079916 cites W2047854407 @default.
• W2040079916 cites W2049177977 @default.
• W2040079916 cites W2049365266 @default.
• W2040079916 cites W2050331574 @default.
• W2040079916 cites W2050429316 @default.
• W2040079916 cites W2051698518 @default.
• W2040079916 cites W2051923099 @default.
• W2040079916 cites W2052162026 @default.
• W2040079916 cites W2056324960 @default.
• W2040079916 cites W2066137743 @default.
• W2040079916 cites W2067170443 @default.
• W2040079916 cites W2067687504 @default.
• W2040079916 cites W2068006175 @default.
• W2040079916 cites W2070395449 @default.
• W2040079916 cites W2071923505 @default.
• W2040079916 cites W2077240787 @default.
• W2040079916 cites W2080715091 @default.
• W2040079916 cites W2080736246 @default.
• W2040079916 cites W2082255480 @default.
• W2040079916 cites W2082872825 @default.
• W2040079916 cites W2085268679 @default.
• W2040079916 cites W2089303501 @default.
• W2040079916 cites W2106878298 @default.
• W2040079916 cites W2110572634 @default.
• W2040079916 cites W2121811422 @default.
• W2040079916 cites W2123146600 @default.
• W2040079916 cites W2129642562 @default.
• W2040079916 cites W2131366640 @default.
• W2040079916 cites W2139673467 @default.
• W2040079916 cites W2142676202 @default.
• W2040079916 cites W2146728293 @default.
• W2040079916 cites W2147286433 @default.
• W2040079916 cites W2148258968 @default.
• W2040079916 cites W2148937565 @default.
• W2040079916 cites W2149540006 @default.
• W2040079916 cites W2151821942 @default.
• W2040079916 cites W2155289192 @default.
• W2040079916 cites W2156871013 @default.
• W2040079916 cites W2162537337 @default.
• W2040079916 cites W2163251531 @default.
• W2040079916 cites W2165481109 @default.
• W2040079916 cites W2170312197 @default.
• W2040079916 cites W2170669019 @default.
• W2040079916 cites W2171180111 @default.
• W2040079916 cites W2171468453 @default.
• W2040079916 cites W2176562570 @default.
• W2040079916 cites W2315091113 @default.
• W2040079916 cites W2316980899 @default.
• W2040079916 cites W2319031739 @default.
• W2040079916 cites W2320613670 @default.
• W2040079916 cites W2326112626 @default.
• W2040079916 cites W2327027326 @default.
• W2040079916 cites W2331215803 @default.
• W2040079916 cites W2949736301 @default.
• W2040079916 cites W2951293693 @default.
• W2040079916 cites W2951326913 @default.
• W2040079916 doi "https://doi.org/10.1021/ar5003208" @default.
• W2040079916 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25511374" @default.
• W2040079916 hasPublicationYear "2014" @default.
• W2040079916 type Work @default.
• W2040079916 sameAs 2040079916 @default.

• next