Iterative approach to enantiopure syn/anti-1,3-polyols via proline-catalyzed sequential alpha-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehydes.
Iterative use of proline-catalyzed tandem alpha-aminoxylation and HWE olefination of aldehydes provided a simple access to 1,3-polyols. The feasibility of this approach is initially studied to synthesize syn- and anti-1,3-diols and is further extended to a syn/syn-1,3,5-triol at a useful level of asymmetric induction and yield. Its usage is illustrated by the short synthesis of a hydroxylactone pheromone component, (2S,3S)-2-hydroxyhexylcyclopentanone.
Kondekar
Nagendra B
NB
Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India.
Kumar
Pradeep
P
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D011108:Polymers; C024617:polyol; D011392:Proline