10.1021/acs.orglett.7b02722.s001
Yasunori Toda
Yasunori
Toda
Shuto Gomyou
Shuto
Gomyou
Shoya Tanaka
Shoya
Tanaka
Yutaka Komiyama
Yutaka
Komiyama
Ayaka Kikuchi
Ayaka
Kikuchi
Hiroyuki Suga
Hiroyuki
Suga
Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones
from Isocyanates and Epoxides
American Chemical Society
2017
Epoxides Preparation
tetraarylphosphonium salts
enantioenriched N
catalyze
ylide
regioselectivity
acid
aryl-substituted oxazolidinones
Isocyanate
role
Br
Tetraarylphosphonium Salt-Catalyzed Synthesis
bifunctional
ønsted
isocyanate
Mechanistic studies
epoxide ring opening
Oxazolidinone
catalyst
TAPS
formation
halohydrin
2017-10-17 16:22:49
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Tetraarylphosphonium_Salt-Catalyzed_Synthesis_of_Oxazolidinones_from_Isocyanates_and_Epoxides/5505829
Preparation of a
range of oxazolidinones, including enantioenriched <i>N</i>-aryl-substituted oxazolidinones, in which tetraarylphosphonium
salts (TAPS) catalyze the [3 + 2] coupling reaction of isocyanates
and epoxides effectively, is described. The key finding is a Brønsted
acid/halide ion bifunctional catalyst that can accelerate epoxide
ring opening with high regioselectivity. Mechanistic studies disclosed
that the ylide generated from TAPS, along with the formation of halohydrins,
plays a crucial role in the reaction with isocyanates.