Copper-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Grignard Reagents.
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چکیده
منابع مشابه
Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents.
A highly efficient method is reported for the asymmetric ring opening of oxabicyclic alkenes with organolithium reagents. Using a copper/chiral phosphoramidite complex together with a Lewis acid (BF(3)·OEt(2)), full selectivity for the anti isomer and excellent enantioselectivities were obtained for the ring opened products.
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Catalyst and substrate studies have been performed on the rhodium-catalyzed asymmetric ring opening reaction. A working model is advanced that involves oxidative insertion with retention to form an organorhodium intermediate that then undergoes nucleophilic attack with inversion. Kinetic and competition experiments have uncovered evidence for a proton transfer step in the catalytic cycle that m...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2005
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo056028g