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Catalytic Asymmetric Synthesis of Stable Oxetenes via Lewis Acid-Promoted [2 + 2] Cycloaddition

Kohsuke Aikawa, Yūta Hioki, Natsumi Shimizu and Koichi Mikami*

*Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan, Email: mikami.k.abm.titech.ac.jp

K. Aikawa, Y. Hioki, N. Shimizu, K. Mikami, J. Am. Chem. Soc., 2011, 133, 20092-20095.

DOI: 10.1021/ja2085299 (free Supporting Information)


Abstract

A dicationic (S)-BINAP-Pd catalyst enables a highly enantioselective and atom-economical [2 + 2] cycloaddition of various alkynes with trifluoropyruvate to yield oxetene derivatives, which can serve as novel chiral building blocks for pharmaceuticals and agrochemicals and can also be transformed into a variety of enantiomerically enriched CF3-substituted compounds.


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Key Words

Oxetenes


ID: J48-Y2011-3600