Organic Letters
Organic Letters
5 years ago

Selective Formation of Functionalized α-Quaternary Malononitriles toward 5,5-Disubstituted Pyrrolopyrimidinones

Selective Formation of Functionalized α-Quaternary Malononitriles toward 5,5-Disubstituted Pyrrolopyrimidinones
Subharekha Raghavan, Yu-hong Lam, Jamie McCabe Dunn, Yong Zhang, Aaron Sun, Melisa Shiroda, John Stelmach, Robert K. Orr, Edward C. Sherer, Sherman T. Waddell, Alan Whitehead
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01930

DOI: 10.1021/acs.orglett.7b01930

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