Diastereoselection in 1,3-O- to -C-alkyl migration reaction of 1-alkenyl alkyl acetals catalyzed by boron trifluoride etherate |
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| Authors: | Mitsuru Takahashi Hiroharu Suzuki Yoshihiko Moro-oka Tsuneo Ikawa |
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| Institution: | Research Laboratory of Resources Utilization, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 227, Japan |
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| Abstract: | Remarkable diastereoselection, with (E)-alkenyl alkyl acetal giving selectively the erythro α-alkyl-β-alkoxyaldehyde, and (Z)-acetal leading preferentially to the threo isomer, is observed in the 1,3-O- to - C-alkyl migration reaction of 1-alkenyl alkyl acetals catalyzed by boron trifluoride etherate. |
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