Asymmetric Cyclization/Nucleophilic Tandem Reaction
of <i>o</i>‑Alkynylacetophenone with (Diazomethyl)phosphonate
for the Synthesis of Functional Isochromenes
Liu Cai
Yuan Chen
Hao Cao
Qi Wei
Yi Yang
Qin Ouyang
Yungui Peng
10.1021/acs.orglett.9b02864.s001
https://acs.figshare.com/articles/journal_contribution/Asymmetric_Cyclization_Nucleophilic_Tandem_Reaction_of_i_o_i_Alkynylacetophenone_with_Diazomethyl_phosphonate_for_the_Synthesis_of_Functional_Isochromenes/9755186
An efficient asymmetric
reaction between (diazomethyl)phosphonate
with <i>o</i>-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.
2019-08-30 19:43:33
diazomethyl
Functional Isochromenes
motif
enantioselectivity
ee
Cyclization
variety
Asymmetric
gain insight
theory calculations
Tandem
enantiomeric
Synthesi
stereocontrol strategy
stereoselectivity
compound
isochromene
Alkynylacetophenone
Diazomethyl
density
tetrasubstituted stereocenters
1- position
alkynylacetophenone