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

被引：10

作者：

Kurosawa, Fumiya ^{[1
]}

Nakano, Takeo ^{[1
]}

Soeta, Takahiro ^{[1
]}

Endo, Kohei ^{[1
]}

Ukaji, Yutaka ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Mat Chem, Kanazawa, Ishikawa 9201192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 11期

基金：

日本学术振兴会;

关键词：

GRIGNARD-REAGENTS; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; BROOK REARRANGEMENT; ALLYLIC ALCOHOLS; Z-ALKENES; VINYL; 1,4-ELIMINATION; FACILE;

D O I：

10.1021/acs.joc.5b00647

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5696 / 5703

页数：8

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