Highly efficient chemical kinetic resolution of bishomoallylic alcohols: synthesis of (R)-sulcatol.
[reaction: see text] A highly efficient chemical kinetic resolution of bishomoallylic alcohols was developed when the alcohols underwent In(OTf)(3)-catalyzed 3,5-oxonium-ene-type cyclization with steroidal aldehyde 2. Consistently high enantiomeric excess (up to >99%) was obtained.
Chen
Shui-Ling
SL
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
Hu
Qi-Ying
QY
Loh
Teck-Peng
TP
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007700:Kinetics; D008968:Molecular Conformation; D015394:Molecular Structure; D000442:Octanols / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000438:Alcohols; D000442:Octanols; C009344:sulcatol