Practical optical resolution of dl-muscone using tartaric acid derivatives as a chiral auxiliary

Add time:08/27/2019    Source:sciencedirect.com

A simple and practical synthesis of (R)-(−)-muscone was achieved by optical resolution of dl-muscone using tartaric acid derivatives. The acetalization of dl-muscone with N,N′-dibenzyl-l-tartaramide in the presence of Sc(OTf)3 and methyl orthoformate furnished a diastereomeric mixture of acetals, which were readily separated by simple recrystallization. Diastereomerically pure acetal was hydrolyzed to give optically pure muscone and recovered N,N′-dibenzyl-l-tartaramide.

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