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Organocatalyst‐Mediated Dynamic Kinetic Enantioselective Acylation of 2‐Chromanols
Author(s) -
Glazier Daniel A.,
Schroeder John M.,
Liu Jitian,
Tang Weiping
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800994
Subject(s) - chemistry , acylation , enantioselective synthesis , kinetic resolution , catalysis , enantiomer , substrate (aquarium) , stereoselectivity , combinatorial chemistry , organocatalysis , organic chemistry , stereochemistry , oceanography , geology
We recently developed a novel chiral catalyst‐directed dynamic kinetic diastereoselective acylation of hemiacetals for the synthesis of carbohydrates. In this update, we describe a catalytic method for the dynamic kinetic enantioselective acylation of 2‐chromanols using benzotetramisole derived catalysts. High yields and enantiomeric excesses were obtained for a broad range of acylated 2‐chromanols, which are important intermediates for the synthesis of various bioactive pharmaceuticals. We hypothesize that the high stereoselectivity of the reaction originates from a novel cation‐ n interaction between the chromanol substrate and the acylated catalyst.