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Exploration of the Mitsunobu Reaction with Tosyl- and Boc-Hydrazones as Nucleophilic Agents

John M. Keith* and Leslie Gomez

*Johnson & Johnson Pharmaceutical Research & Development, L.L.C., 3210 Merryfield Row, San Diego, California 92121, Email: jkeithprdus.jnj.com

J. M. Keith, L. Gomez, J. Org. Chem., 2006, 71, 7113-7116.

DOI: 10.1021/jo061185g (free Supporting Information)


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Abstract

Tosyl- and Boc-hydrazones were found to be effective nucleophiles in the Mitsunobu reaction. Tosyl hydrazones reacted cleanly with primary and secondary alcohols when co-administered to a cooled DBAD/PPh3 or DEAD/PPh3 complex.

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Key Words

Mitsunobu Reaction, Hydrazones


ID: J42-Y2006-2860