Open AccessNew Practical Synthesis of the Exceptional Musk Odorants (R)-Muscone and (R,Z)-5-Muscenone
Author(s) -
Oliver Knopff,
Jérôme Kuhne
Publication year - 2008
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2008.489
Subject(s) - aldol reaction , enantioselective synthesis , kinetic resolution , aldol condensation , chemistry , stereochemistry , organic chemistry , catalysis
Herein we describe a short and practical synthesis of the exceptional musk odorants (R)-muscone and (R,Z)-5-muscenone from a readily available achiral macrocyclic diketone. The key step of the synthesis is the first sodium N-methylephedrate mediated enantioselective aldol condensation reaction (up to 76% ee). This new type of reaction proceeds via a dynamic kinetic resolution of an aldol intermediate.