Desymmetrization of cyclic anhydrides mediated by cinchona alkaloids: synthesis and olfactory properties of new fragrances based on (R)- and (S)-2-ethylhexanol.
A series of enantiomerically pure new fragrances, derived from 2-ethylhexanol, have been prepared and their olfactory properties evaluated. The key step of the synthesis is cinchona-alkaloid-catalyzed desymmetrization of cyclic meso-anhydrides with (R)- and (S)-2-ethylhexanol and proceeded in good to excellent diastereoselectivities (92:8-98:2 dr). Enantiomerically pure alcohols were prepared by lipase-catalyzed kinetic resolution of 2-ethylhexanol using vinyl laurate as acyl donor.
Cisko-Anić
Blazenka
B
R&D, Saponia d.d., Osijek, Croatia.
Hamersak
Zdenko
Z
D000812:Anhydrides / Q000378:metabolism*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000378:metabolism*; D003500:Cyclization; D006586:Hexanes / Q000737:chemistry; D000441:Hexanols / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000378:metabolism; D015394:Molecular Structure; D010476:Perfume / Q000138:chemical synthesis* / Q000378:metabolism*; D012903:Smell; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature
D000812:Anhydrides; D002930:Cinchona Alkaloids; D006586:Hexanes; D000441:Hexanols; D010476:Perfume; D008049:Lipase; C034017:2-ethylhexanol