Gold-catalyzed waste-free generation and reaction of azomethine ylides: Internal redox/dipolar cycloaddition cascade

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초록

(Chemical Equation Presented) High-octane synthesis: Azomethine ylides can be generated from an internal redox reaction of a nitrone-tethered alkyne under electrophilic metal catalysis (see scheme; M=metal). This novel and atom-economical generation of an azomethine ylide does not involve potentially explosive diazo derivatives. The azomethine ylide can participate in a dipolar cycloaddition cascade to provide an azabicyclo[3.2.1]octane.

키워드

azomethine ylidescarbenescyclizationhomogeneous catalysisredox chemistry1,3-DIPOLAR CYCLOADDITIONSYNTHETIC ACCESSDERIVATIVESCYCLIZATIONINSERTIONACTIVATIONCOMPLEXESALKALOIDSTANDEM
제목
Gold-catalyzed waste-free generation and reaction of azomethine ylides: Internal redox/dipolar cycloaddition cascade
저자
Yeom, Hyttn-SukLee, Ji-EunShin, Setinghoon
DOI
10.1002/anie.200802802
발행일
2008-09
유형
Article
저널명
Angewandte Chemie - International Edition
47
37
페이지
7040 ~ 7043