Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol

Huiles essentielles et chiralité moléculaire

“…Son odeur florale de rose rappelle celle de l'huile de géranium alors que l'arôme du (R)-(+)-Citronellol est semblable à l'huile de citronnelle. Leurs seuils olfactifs sont proches entre 40-50 ppb pour l'énantiomère (S) et 50 ppb pour le (R) [51,52].…”

Enantioselective Synthesis of Cyclopropanes via CuH-Catalyzed Intramolecular Hydroalkylation

“…trans -1,2-Disubstituted cyclopropanes are a common structural motif found in numerous biologically active compounds due to their unique reactivity, constrained conformational flexibility, and enhanced metabolic stability that they confer to drug molecules . While the Simmons–Smith cyclopropanation is a well-established transformation to access such a motif, catalytic asymmetric variants of this reaction are relatively scarce. − In contrast, well-established methods for the synthesis of chiral cyclopropanes in an enantioselective manner involve the addition of metallocarbenes into CC bonds with diazo compounds (Figure A). − Another approach is the use of asymmetric Michael addition-initiated ring closure reactions (MIRC, e.g., Corey–Chaykovsky reaction), but while this strategy has been exploited within the domain of organocatalysis, it remains relatively unexplored in transition metal catalysis (Figure A). Overall, despite the availability of various methods for accessing cyclopropanes, recent research from industrial groups underscores the necessity of exploring new chemical avenues in this direction …”