jo9b01611_si_002.cif (1.37 MB)
One-Pot Synthesis of Enantiopure Spiro[3,4-dihydrobenzo[b][1,4]oxazine-2,3′-oxindole] via Regio- and Stereoselective Tandem Ring Opening/Cyclization of Spiroaziridine Oxindoles with Bromophenols
dataset
posted on 2019-07-30, 14:47 authored by Saumen Hajra, Atanu Hazra, SK Abu SalehA highly efficient regio- and stereoselective
spiroaziridine ring
opening with 2-bromophenols and a subsequent tandem cyclization reaction
was developed for the one-pot synthesis of enantiopure 3,4-dihydrospiro[benzo[b][1,4]oxazine-2,3′-oxindole] with excellent enantiopurity
(ee up to >99%). It is further extended to asymmetric synthesis
of
NH-free 3,4-dihydrospiro[benzo[b][1,4]oxazine-2,3′-xindole]
retaining the optical activity.