Tetrahedron (2020)
Update date:2022-08-26
Topics:
Nemcsok, Tamás
Rapi, Zsolt
Bagi, Péter
Guan, Ying Hou
Orbán, István
Keglevich, Gy?rgy
Bakó, Péter
A few new D-galactose- and D-glucose-based monoaza-15-crown-5 type lariat ethers have been synthesized. These macrocycles and their derivatives proved to be efficient catalysts in the cyclopropanation of (E)-3-phenyl-2-(phenylsulfonyl)acrylonitrile performed with diethyl bromomalonate under mild phase transfer conditions. Among the catalysts tested, the macrocycle having methyl α-D-galactopyranoside unit generated the highest asymmetric induction (80% ee). In the reactions of the aryl-substituted phenylsulfonyl-acrylonitrile derivatives, the cyclopropanation of the meta- and para-substituted starting materials took place with high ee values (75–84% ee). The cyclopropane derivatives synthesized from analogous α,β-unsaturated cyanosulfones containing naphthyl, pyridyl, furyl and thienyl groups were obtained with enantioselectivities up to 85%, and in excellent yields.
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Doi:10.1016/j.phytol.2020.03.001
(2020)Doi:10.1002/zaac.200500247
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