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Asymmetric Intramolecular Rauhut-Currier Reaction and Its Desymmetric Version via Double Thiol/Phase-Transfer
Ying Jiang1, Yang Yang1, Qing He1
1Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Abstract:
An asymmetric intramolecular Rauhut-Currier reaction of linear bis(enones) has been achieved via double activation catalysis of thiols and phase transfer substances, furnishing both enantioenriched cyclohexene and cyclopentene derivatives (up to 95% ee). Furthermore, the desymmetric version of prochiral substrates was developed under similar catalysis, producing the frameworks bearing an additional tertiary or even quaternary stereogenic center with moderate to excellent diastereo- and enantioselectivity (up to 95% ee, >19:1 dr).
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