ol7b01930_si_001.cif (52.48 kB)
Selective Formation of Functionalized α‑Quaternary Malononitriles toward 5,5-Disubstituted Pyrrolopyrimidinones
dataset
posted on 2017-08-16, 13:23 authored by Alan Whitehead, Yong Zhang, Jamie McCabe Dunn, Edward C. Sherer, Yu-hong Lam, John Stelmach, Aaron Sun, Melisa Shiroda, Robert K. Orr, Sherman T. Waddell, Subharekha RaghavanA modular, selective
approach to complex α-tertiary substituted
malononitriles is reported. The method takes advantage of β-ester-substituted
α,α-dinitrile alkenes as highly reactive, chemoselective
electrophiles for 1,4-additions with organometallic nucleophiles to
produce functionally and sterically dense all-carbon quaternary centers.
In the presence of a chiral ester auxiliary bearing an aromatic ring,
the 1,4-addition occurs with good to excellent selectivity due to
favorable cation−π interactions. The highly functionalized
malononitriles represent versatile building blocks and can be applied
toward efficient, highly selective syntheses of 5,5-disubstituted
pyrrolopyrimidinones.
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pyrrolopyrimidinonechiral esterpresenceselectivityPyrrolopyrimidinonechemoselective electrophilesbuilding blocksfunctionalized malononitrilesorganometallic nucleophilesstericallyreactiveβ-approachmethodalkeneMalononitriledinitrileSelective FormationsyntheseDisubstitutedQuaternarycationinteractionFunctionalizedall-carbon quaternary centersester-substituteddisubstitutedα-
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