The first organocatalyzed phase-transfer enantioselective conjugate addition of cyanide ion derived from acetone cyanohydrin to beta,beta'-disubstituted nitroolefins is reported. The reaction leads to the efficient formation of nitroalkanes bearing an all-carbon quaternary stereogenic center in up to 72% ee.
Organocatalyzed Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers through Conjugate Addition of Acetone Cyanohydrin / Bernardi, Luca; Fini, Francesco; Fochi, Mariafrancesca; Ricci, Alfredo. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 2008:12(2008), pp. 1857-1861. [10.1055/s-2008-1078496]
Organocatalyzed Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers through Conjugate Addition of Acetone Cyanohydrin
FINI, Francesco;
2008
Abstract
The first organocatalyzed phase-transfer enantioselective conjugate addition of cyanide ion derived from acetone cyanohydrin to beta,beta'-disubstituted nitroolefins is reported. The reaction leads to the efficient formation of nitroalkanes bearing an all-carbon quaternary stereogenic center in up to 72% ee.
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