Merck
CN
  • Mechanism of the regio- and diastereoselective ring expansion reaction using trimethylsilyldiazomethane.

Mechanism of the regio- and diastereoselective ring expansion reaction using trimethylsilyldiazomethane.

Organic letters (2012-08-21)
Takeo Sakai, Satoshi Ito, Hiroki Furuta, Yuki Kawahara, Yuji Mori
摘要

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.