Synthesis of 8-Oxabicyclo[3.2.1]octanes

Synthesis of 8-Oxabicyclo[3.2.1]octanes by TiCl4-mediated activation of TiCl4-Mediated Reactions of 3-Alkoxycyclobutanones and Allenylsilanes: T. Onnagawa, M. Yamazaki, T. Yoshimura, J-i. Matsuo
Synlett 2018, DOI: 10.1055/s-0037-1611276


8-Oxabicyclo[3.2.1]octanes are useful synthetic intermediates in organic synthesis, which can be stereospecifically transformed into chiral monocyclic or linear compounds by means of different ring-opening reactions. In an important contribution to the field, the group of Professor Jun-ichi Matsuo (Kanazawa University, Japan) has now described a novel multi-step process that relies on a TiCl4-mediated activation of 3-alkoxycyclobutanones and subsequent reaction with allenylsilanes.

Professor Matsuo said: “Synthetically useful 8-oxabicyclo[3.2.1]octan-3-ones were stereoselectively synthesized from readily available simple building blocks, 3-alkoxycyclobutanones and allenylsilanes, through a unique multi-step reaction mechanism.”
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