TY - JOUR
T1 - Ozone Oxidation of Silylalkene
T2 - Mechanistic Study and Application for the Synthesis of Silacarboxylic Acid Derivatives
AU - Igawa, Kazunobu
AU - Kawasaki, Yuuya
AU - Nozaki, Sora
AU - Kokan, Naoto
AU - Tomooka, Katsuhiko
N1 - Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/3/20
Y1 - 2020/3/20
N2 - The addition-type ozone oxidation of silylalkenes is a highly efficient reaction to provide synthetically versatile α-silylperoxy carbonyl compounds. To gain insight into the reaction mechanism, we performed a computational study, which revealed that the reaction proceeds via [1,2]-Brook rearrangement-type silyl migration of primary ozonide. In sharp contrast to the addition-type reactions, the ozone oxidation of α-alkoxysilylalkenes proceeds in a cleavage-type manner to afford excellent yields of silacarboxylic acid esters via the 1,3-cycloelimination of primary ozonide prior to 1,2-silyl migration.
AB - The addition-type ozone oxidation of silylalkenes is a highly efficient reaction to provide synthetically versatile α-silylperoxy carbonyl compounds. To gain insight into the reaction mechanism, we performed a computational study, which revealed that the reaction proceeds via [1,2]-Brook rearrangement-type silyl migration of primary ozonide. In sharp contrast to the addition-type reactions, the ozone oxidation of α-alkoxysilylalkenes proceeds in a cleavage-type manner to afford excellent yields of silacarboxylic acid esters via the 1,3-cycloelimination of primary ozonide prior to 1,2-silyl migration.
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U2 - 10.1021/acs.joc.9b03350
DO - 10.1021/acs.joc.9b03350
M3 - Article
C2 - 32141746
AN - SCOPUS:85081664186
SN - 0022-3263
VL - 85
SP - 4165
EP - 4171
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -