3 years ago

Switchable Chemoselectivity for Organocatalytic, Asymmetric Malononitrile Addition to ortho-Formyl Chalcones

Switchable Chemoselectivity for Organocatalytic, Asymmetric Malononitrile Addition to ortho-Formyl Chalcones
Gurupada Hazra, Prasanta Ghorai, Sanjay Maity, Mithu Saha
Chemoselective 1,2- and 1,4-addition of malononitriles to ortho-formyl chalcones using cinchona alkaloid based bifunctional chiral organocatalysts has been shown by tuning the electronic nature of the malononitriles. Alkyl (hard) malononitriles undergo an asymmetric 1,2-addition followed by oxa-Michael reaction cascade to afford 1,3-disubstituted isobenzofurans with high enantio- and diastereoselectivity. Aryl (soft) malononitriles proceed through 1,4-addition followed by an aldol reaction cascade to provide indanols, having three consecutive stereocenters, in good yields and with good to excellent enantio- and diastereoselectivites.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02862

DOI: 10.1021/acs.orglett.7b02862

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