Fluoroanthracenylmethyl cinchonidine

For many years applications of the Bradsher reaction were restricted due to its limited substrate scope and requirement for harsh reaction conditions. However, after the advancement of the arene oxide concept concerning the metabolism of polycyclic aromatic hydrocarbons, synthesis of all the nuclear monohydroxylated derivatives of 7,12-dimethylbenz[a]-anthracene (DMBA), diol epoxide metabolites of DMBA, and fluoro derivatives of DMBA was undertaken for carcinogenicity and mutagenicity determination studies. " Interest in the Bradsher reaction has increased greatly as a consequence of the need to construct these polycyclic aromatic hydrocarbons. Development of fluoroanthracenylmethyl cinchonidine as an efficient phase-transfer catalyst for asymmetric glycine alkylation also expanded the scope of the Bradsher reaction. ... 

Andrus and co-workers developed fluoroanthracenylmethyl cinchonidine 57 as an efficient phase-transfer catalyst, and it was explored for asymmetric glycine alkylation." The fluoroanthracenylmethyl precursor was synthesized from an aryloxazolidinone and aldehyde using the Bradsher reaction in the key step. This cinehonidine eatalyst promotes... 

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See also in sourсe #XX -- [ ]

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