Enantioselective Dehydroxyhydrogenation of 3-Indolylmethanols by the Combined Use of Benzothiazoline and Chiral Phosphoric Acid: Construction of a Tertiary Carbon Center
Hiroto Osakabe, Shota Saito, Masamichi Miyagawa, Takuya Suga, Tatsuhiro Uchikura, Takahiko Akiyama
Abstract
The chiral indole is an important structure in organic chemistry. We have developed an enantioselective hydrogen transfer reaction of indolylmethanol, which is characterized by the combined use of benzothiazoline and a newly synthesized chiral phosphoric acid. The reaction furnished indoles bearing a chiral tertiary carbon center at the 3-position in high to excellent yields and with excellent enantioselectivities, most of which are greater than 95% ee. The chiral indole was converted into an inhibitor of leukotriene production while retaining excellent ee.
Topics & Concepts
Enantioselective synthesisChemistryPhosphoric acidAsymmetric carbonIndole testCarbon fibersOrganic chemistryCenter (category theory)Medicinal chemistryCatalysisOptically activeMathematicsComposite numberAlgorithmCrystallographySynthesis of Indole DerivativesAsymmetric Synthesis and CatalysisChemical Synthesis and Reactions