Transition Metal-Mediated Transformation of Ynamides and Application to Organic Synthesis
-
- Saito Nozomi
- Meiji Pharmaceutical University
-
- Sato Yoshihiro
- Faculty of Pharmaceutical Sciences, Hokkaido University
Bibliographic Information
- Other Title
-
- 遷移金属錯体を利用したイナミドの新規分子変換反応の開発と応用研究
- センイ キンゾク サクタイ オ リヨウ シタ イナミド ノ シンキ ブンシ ヘンカン ハンノウ ノ カイハツ ト オウヨウ ケンキュウ
Search this article
Description
<p>N-Alkynylamide (ynamide) is recognized as a polarized alkyne, due to the delocalization of lone-pair electrons on the nitrogen atom to the carbon-carbon triple bond, and it is widely used in recent organic synthesis. We conducted the studies on the efficient and useful molecular transformation of ynamides with transition metal catalysis, and several new methods of ynamide transformation were developed. First, we demonstrated new synthetic protocol of enamide from ynamide. Thus, γ-siloxyenmides were efficiently prepared by the nickel(0)-catalyzed regio- and stereoselective coupling of ynamide, aldehyde and silane. Moreover, regioselective synthesis of tri- and tetra-substituted enamides was achieved by palladium-catalyzed silaboration of ynamide. On the other hand, 2-amino-1,3-dinenes were synthesized by ruthenium-catalyzed formal hydrovinylation of ynamide with ethylene. Carboxylation of ynamide with CO2 mediated by nickel(0) complex gave α-substituted-β-aminoacrylate, which was transformed into β2-amino acid derivative in a enantioselective manner by rhodium-catalyzed asymmetric hydrogenation. Finally, the first total synthesis of (−)-herbindoles A, B and C was achieved by [2+2+2] cyclization of dialkynylynamide.</p>
Journal
-
- Journal of Synthetic Organic Chemistry, Japan
-
Journal of Synthetic Organic Chemistry, Japan 76 (7), 699-709, 2018-07-01
The Society of Synthetic Organic Chemistry, Japan
- Tweet
Keywords
Details 詳細情報について
-
- CRID
- 1390282763019603072
-
- NII Article ID
- 130007403452
-
- NII Book ID
- AN0024521X
-
- ISSN
- 18836526
- 00379980
-
- NDL BIB ID
- 029156869
-
- Text Lang
- ja
-
- Data Source
-
- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
-
- Abstract License Flag
- Disallowed