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Silylative Cyclopropanation of Allyl Phosphates with Silylboronates
Author(s) -
Shintani Ryo,
Fujie Ryuhei,
Takeda Momotaro,
Nozaki Kyoko
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403726
Subject(s) - cyclopropanation , allylic rearrangement , nucleophile , chemistry , amide , medicinal chemistry , potassium , trimethylsilyl , catalysis , organic chemistry
Abstract 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.