Practical and efficient multigram preparation of a camphor-derived diol for the enantioselective Lewis acid catalyzed allylboration of aldehydes.
[reaction: see text] Chiral diols are important molecules with widespread use as chiral auxiliaries and ligands in enantioselective synthesis. Therefore, efficient and practical syntheses of highly dissymmetrical nonracemic diols are still a meaningful pursuit. Two new routes to access camphor-derived chiral diol 1 have been developed. One route employs camphorquinone (3) as the starting material, affording in only two steps the desired diol in 55% overall yield. The second route, from camphor (2), leads to the desired diol in an efficient four-step synthesis, with an overall yield of 55%.
Lachance
Hugo
H
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
St-Onge
Miguel
M
Hall
Dennis G
DG
D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002164:Camphor / Q000737:chemistry*; D002384:Catalysis; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D000498:Allyl Compounds; D001896:Boron Compounds; D002164:Camphor