Mechanism of the regio- and diastereoselective ring expansion reaction using trimethylsilyldiazomethane.
An equatorial attack of TMS-diazomethane was determined to be the first step of the BF(3)-promoted ring expansion reaction of six-membered ketones using TMS-diazomethane. The migration reaction occurred in a conformation in which the carbonyl oxygen and the TMS group were antiperiplanar to predominantly afford trans-seven-membered ketones.
Faculty of Pharmacy, Meijo University, Nagoya, 468-8503, Japan.
Takeo
T
Sakai
Satoshi
S
Ito
Hiroki
H
Furuta
Yuki
Y
Kawahara
Yuji
Y
Mori
D003978:Diazomethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D007659:Ketones; D014297:Trimethylsilyl Compounds; D003978:Diazomethane; C060070:trimethylsilyldiazomethane