Selective Formation of Functionalized α‑Quaternary
Malononitriles toward 5,5-Disubstituted Pyrrolopyrimidinones
Posted on 2017-08-16 - 13:23
A 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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Whitehead, Alan; Zhang, Yong; McCabe Dunn, Jamie; Sherer, Edward C.; Lam, Yu-hong; Stelmach, John; et al. (2017). Selective Formation of Functionalized α‑Quaternary
Malononitriles toward 5,5-Disubstituted Pyrrolopyrimidinones. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b01930
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AUTHORS (11)
AW
Alan Whitehead
YZ
Yong Zhang
JM
Jamie McCabe Dunn
ES
Edward C. Sherer
YL
Yu-hong Lam
JS
John Stelmach
AS
Aaron Sun
MS
Melisa Shiroda
RO
Robert K. Orr
SW
Sherman T. Waddell
SR
Subharekha Raghavan
KEYWORDS
pyrrolopyrimidinonechiral esterpresenceselectivityPyrrolopyrimidinonechemoselective electrophilesbuilding blocksfunctionalized malononitrilesorganometallic nucleophilesstericallyreactiveβ-approachmethodalkeneMalononitriledinitrileSelective FormationsyntheseDisubstitutedQuaternarycationinteractionFunctionalizedall-carbon quaternary centersester-substituteddisubstitutedα-