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Synthesis And Application Of Novel Chiral Ionic Liquids Derived From Alpha-Pinene, Yun Wang

Theses

Two new chiral ionic liquids of oxazolinium cations derived from a-pinene: 9,9-Dimethyl-4-propenyl-5-propyl-3 -oxa-5-azonia-tricyclo [6.1.1.0 ^2,6] dec-4-ene tetrafluoro borate ([ChIPOZ] [BF₄]) and 9,9-Dimethyl-4-propenyl-5-propyl-3-oxa-5-azonia-tricyclo [6.1.1.0 ^2,6] dec-4-ene hexafluoro phosphate ([ChIPOZ][PF₆]). Both these chiral ionic liquids have been applied in enantiomeric copper-catalyzed 1,4-addition reactions with diethyl zinc. The enantiomeric excess for product using [ChIPOZ][BF₄] is above 70% and for [ChIPOZ][PF₆] is above 30%. Chiral ionic liquids worked as phase transfer catalysts In this reaction.

α-Pinene was used as the "chiral pool" in the synthesis of amino alcohol through a two-step reaction, followed by …