タンデム6pi電環化とニトロジエンのサイクル添加により,多循環性ニトロゾアセタルが得られる

Gardner S Creech¹, Ohyun Kwon

¹Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.

Journal of the American Chemical Society

|June 19, 2010

まとめ

ニトロジエンはドミノ反応を経て,機能化されたニトロソアセタルを生成する. これらの化合物は,価値あるヒドロキシアミドとアミノ酸に変換することができます.

科学分野:

有機化学オーガニック・ケミストリー
合成化学合成化学とは

背景:

ニトロジエンは,多用途の有機化合物である.
電気サイクリング反応は,有機合成における重要な変換である.

研究の目的:

高機能なニトロソアセタルを合成するための新しい1ポット,2段階のドミノプロセスを開発する.
局所生成のニトロナートによる [3 + 2] 二極サイクロアディションの範囲と選択性を調査する.
選択的水解分解によって合成されたニトロゾアセタルの有用性を実証する.

主な方法:

ニトロジエンの熱的再配置は6π電環化による.
タンデム [3 + 2] 二極性サイクロアディションで,様々な二極性を持つ.
ニトロアセタール製品の選択的水解.

主要な成果:

ドミノプロセスは,優れた顔面およびエクソ選択性を持つ高度に機能化されたニトロゾアセタルを効率的に生成します.
電子が豊富で,中性で,欠乏的な二極性体の幅広い範囲は,サイクロアディションと互換性があります.
選択的水解は,密度の高い機能を持つスパイロサイクルのヒドロキシアミドとヒドロキシガンマアミノ酸へのアクセスを提供します.

結論:

開発されたドミノ反応は,複雑なニトロソアセタールへの強力で効率的な経路を提供します.
合成されたニトロソアセタルは,スパイロサイクルヒドロキシアミドやガンマアミノ酸を含む多様な機能性分子のための貴重な前駆体として機能します.

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