p-Menthane-3-carboxaldehyde: a useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity.
(+)- or (-)-p-Menthane-3-carboxaldehyde is made in two easy steps from (+)- or (-)-menthone, respectively. This auxiliary allows for the synthesis of carbonyl compounds bearing a alpha-chiral quaternary carbon. The flexibility, efficiency, and ease of use of the method are demonstrated in a series of examples, which include the total synthesis of (+)-cuparenone as well as a partial synthesis of (-)-cassiol.
Spino
Claude
C
Université de Sherbrooke, Département de Chimie, 2500 Boul. Université, Sherbrooke, Qc, Canada, J1K 2R1. Claude.Spino@USherbrooke.ca
Godbout
Cédrickx
C
Beaulieu
Christian
C
Harter
Magali
M
Mwene-Mbeja
Topwe M
TM
Boisvert
Luc
L
D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis*; D008610:Menthol / Q000031:analogs & derivatives* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D000596:Amino Acids; D012717:Sesquiterpenes; D008610:Menthol