Wolff-Staudinger Cascade Reaction ウォルフ-シュタウディンガー カスケード反応


Synthesis, 201648, 3515-3526.

“Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff–Staudinger Cascade Reaction”

B. Musio, F. Mariani, E. P. Śliwiński, M. A. Kabeshov, H. Odajima, S. V. Ley

  A new, single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of α-diazoketones at high temperature. A number of amides and β-lactams were obtained by ketene generation in situ and reaction with amines and imines, respectively, in good to excellent yields. The preferential formation of trans-configured β-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported, and a new web-based molecular viewer, which takes advantage from Augmented Reality (AR) technology, is also described for a faster interpretation of computed data.

Supporting Information

Equipment information Reactor size: 100 mm, Maximum power: 100 W (SAIDA FDS INC.)


装置情報:100 mmキャビティ、100W