jo7b01860_si_002.cif (844.18 kB)
4‑Diazoisochroman-3-imines: A Class of Metal Carbene Precursors for the Synthesis of Isochromene Derivatives
dataset
posted on 2017-09-27, 00:00 authored by Anni Ren, Bo Lang, Jialun Lin, Ping Lu, Yanguang Wang4-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.