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Stereoselective Synthesis of Styrene Oxides via a Mitsunobu Cyclodehydration

Steven A. Weissman*, Kai Rossen and Paul J. Reider

*Department of Process Research, Merck & Co., Inc, Rahway, New Jersey 07065

S. A. Weissman, K. Rossen, P. J. Reider, Org. Lett., 2001, 3, 2513-2513.

DOI: 10.1021/ol016167u

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The Mitsunobu cyclodehydration of chiral phenethane-1,2-diols, readily accessed from styrene derivatives, provides the corresponding styrene oxides with high levels of stereoretention for electron-poor substrates. The combination of tricyclohexylphosphine and diisopropylazodicarboxylate in THF provides the best results.

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Key Words

Mitsunobu reaction, epoxides

ID: J54-Y2001