Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6 Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade

Yeom, Hyun-Suk; Lee, Youngun; Jeong, Jaewon; So, Eunsoo; Hwang, Soojin; Lee, Ji-Eun; Lee, Shim Sung; Shin, Seunghoon

doi:10.1002/anie.200906346

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Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6 Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade

Yeom, Hyun-Suk;
Lee, Youngun;
Jeong, Jaewon;
So, Eunsoo;
Hwang, Soojin;
... Shin, Seunghoon;
외 2명

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초록

"Chemical Equation Presented" Just another Mannich Monday: A cascade intramolecular redox-pinacol-Mannich-Michael reaction sequence catalyzed by gold complexes can be used to generate a variety of structures including spirocycles, 1-aminoindanes, and 5,6-fused azabicycles that have a quaternary carbon center. The reaction is characterized by complete atom-economy, high diastereoselectivity, and remarkable efficiency through tandem reactions.

키워드

carbenoids; cascade reactions; gold; Mannich reactions; redox chemistry; TRANSFER HYDROGENATION; 3-COMPONENT REACTION; CARBONYL-COMPOUNDS; ORGANIC-SYNTHESIS; TANDEM REACTION; AU CATALYSIS; PI-ACIDS; GENERATION; YLIDES; CYCLOISOMERIZATION

제목: Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6 Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade

저자: Yeom, Hyun-Suk; Lee, Youngun; Jeong, Jaewon; So, Eunsoo; Hwang, Soojin; Lee, Ji-Eun; Lee, Shim Sung; Shin, Seunghoon

DOI: 10.1002/anie.200906346

발행일: 2010-02

유형: Article

저널명: Angewandte Chemie - International Edition

권: 49

호: 9

페이지: 1611 ~ 1614