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(Z)-Selective Enol Triflation of α-Alkoxyacetoaldehydes: Application to Synthesis of (Z)-Allylic Alcohols via Cross-Coupling Reaction and [1,2]-Wittig Rearrangement

Fumiya Kurosawa, Takeo Nakano, Takahiro Soeta, Kohei Endo and Yutaka Ukaji*

*Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan, Email: ukajistaff.kanazawa-u.ac.jp

F. Kurosawa, T. Nakano, T. Soeta, K. Endo, U. Ukaji, J. Org. Chem., 2015, 80, 5696-5703.

DOI: 10.1021/acs.joc.5b00647 (free Supporting Information)


 

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Abstract

A stereoselective transformation of α-alkoxyacetoaldehydes gives the corresponding β-alkoxy vinyl triflates by treatment with phenyl triflimide and DBU. Subsequent transition metal-catalyzed cross-coupling reactions followed by  [1,2]-Wittig rearrangements enable the stereoselective synthesis of structurally diverse (Z)-allylic alcohols.

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Key Words

[1,2]-Wittig Rearrangements, allylic alcohols


ID: J42-Y2015