Total synthesis of (R)-(−)-actisonitrile via O-alkylation of optically active 4-hydroxymethyloxazolidin-2-one derivative

Add time:07/25/2019    Source:sciencedirect.com

The enantioselective synthesis of (R)-(−)-actisonitrile 1 has been achieved via O-alkylation of (4R,αS)-4-hydroxymethyl-3-(α-methylbenzyl)oxazolidin-2-one (αS)-4 with 1-iodohexadecane in the presence of CsOH in DMF. Under these reaction conditions, the O-alkylation was much faster than the intramolecular acyl transfer of (αS)-4.

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