title: Remote Asymmetric Induction Using Acetate-Type Vinylketene Silyl N,O-Acetals.
abstract: 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 SnCl4and 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.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University , 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
authors.forename: Naoya
authors.initials: N
authors.lastname: Sagawa
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University , 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
authors.forename: Haruka
authors.initials: H
authors.lastname: Sato
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University , 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
authors.forename: Seijiro
authors.identifier: 0000-0002-8036-532X
authors.initials: S
authors.lastname: Hosokawa