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

作者：Kurosawa Fumiya; Nakano Takeo; Soeta Takahiro; Endo Kohei; Ukaji Yutaka^*

来源：Journal of Organic Chemistry, 2015, 80(11): 5696-5703.

DOI：10.1021/acs.joc.5b00647

The stereoselective transformation of alpha-alkoxyacetoaldehydes to the corresponding (Z)-vinyl triflates was achieved by treatment with phenyl triflimide and DBU. The stereochemistry was explained by the "syn-effect," which was attributed primarily to an sigma -> pi* interaction. The,beta-alkoxy vinyl triflates obtained were applied to the stereoselective synthesis of structurally diverse (Z)-allylic alcohols via transition metal-catalyzed cross-coupling reaction and [1,2]-Wittig rearrangement.

• 出版日期2015-6-5