Efficient intramolecular asymmetric reductions of alpha-, beta-, and gamma-keto acids with diisopinocampheylborane.
[figure: see text] alpha-, beta-, and gamma-Keto acids are reduced with diisopinocampheylborane at room temperature to the corresponding hydroxy acids with predictable stereochemistry in very high ee. The gamma-hydroxy acids produced were conveniently cyclized to the corresponding lactones. This provides a simple synthesis of 4-hexanolide, a component of the pheromone secreted by the female dermestid beetle Trogoderma glabrum.
Ramachandran
P V
PV
Herbert C. Brown Center for Borane Research, Purdue University, West Lafayette, Indiana 47907-1393, USA. chandran@purdue.edu
Brown
H C
HC
Pitre
S
S
D000818:Animals; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D001517:Coleoptera; D005260:Female; D007651:Keto Acids / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D010675:Pheromones / Q000737:chemistry / Q000378:metabolism
D001896:Boron Compounds; D007651:Keto Acids; D007783:Lactones; D010675:Pheromones; C430364:4-hexanolide