ol9b02864_si_001.pdf (11.73 MB)
Asymmetric Cyclization/Nucleophilic Tandem Reaction of o‑Alkynylacetophenone with (Diazomethyl)phosphonate for the Synthesis of Functional Isochromenes
journal contribution
posted on 2019-08-30, 19:43 authored by Liu Cai, Yuan Chen, Hao Cao, Qi Wei, Yi Yang, Qin Ouyang, Yungui PengAn efficient asymmetric
reaction between (diazomethyl)phosphonate
with o-alkynylacetophenone has been established by
employing different stereocontrol strategy. A variety of isochromenes
bearing tetrasubstituted stereocenters and (diazomethyl)phosphonate
at the 1-position were prepared in yield up to 99% with enantioselectivity
up to 94% enantiomeric excess (ee) for the first time. These functional
isochromenes could be transformed to important structural motifs in
biologically active compounds. Moreover, density functional theory
calculations were conducted to gain insight into the process and the
stereoselectivity.