American Chemical Society
ol6b03476_si_001.cif (703.73 kB)

Remote Asymmetric Induction Using Acetate-Type Vinylketene Silyl N,O‑Acetals

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posted on 2016-12-13, 16:10 authored by Naoya Sagawa, Haruka Sato, Seijiro Hosokawa
Remote asymmetric induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived from crotonate and l-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl4 and BF3·OEt2, respectively. The SnCl4-mediated isomerization of silyl dienol ether was found, and the resulting major isomer showed high reactivity to give γ-adduct in high stereoselectivity.