Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

4-Diazoisochroman-3-imines: A Class of Metal Carbene Precursors for the Synthesis of Isochromene Derivatives

4-Diazoisochroman-3-imines: A Class of Metal Carbene Precursors for the Synthesis of Isochromene Derivatives
Anni Ren, Ping Lu, Yanguang Wang, Jialun Lin, Bo Lang
4-Diazoisochroman-3-imines were investigated for their synthetic applications as a new class of metal carbene precursors. Under the catalysis from a Rh(II) complex, this class of α-diazo imidates reacted with alkenes and conjugated dienes through a formal [2 + 1] (i.e., cyclopropanation) or [4 + 3] cycloaddition to furnish spiro[cyclopropane-1,4′-isochroman]-3′-imines and tetrahydroisochromeno[3,4-b] azepines, respectively. When Rh(II)/AgOTf was used as cocatalyst, the formal [3 + 2] cycloaddition of 4-diazoisochroman-3-imines with terminal alkynes took place, leading to the synthesis of 2-aryl-3,5-dihydroisochromeno[3,4-b]pyrroles.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01860

DOI: 10.1021/acs.joc.7b01860

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