Silylative cyclopropanation of allyl phosphates with silylboronates.
A potassium-bis(trimethylsilyl)amide-mediated cyclopropanation of allyl phosphates with silylboronates has been developed. Unlike the reported copper-catalyzed allylic substitution reactions, the nucleophile selectively attacks at the β-position of the allylic substrates under the present reaction conditions. The mechanism of this process has also been investigated, thus indicating the involvement of a silylpotassium species as the active nucleophilic component.
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan). shintani@chembio.t.u-tokyo.ac.jp.
Ryo
R
Shintani
Ryuhei
R
Fujie
Momotaro
M
Takeda
Kyoko
K
Nozaki
reaction mechanisms; rearrangement; silanes; small ring system; synthetic methods