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Dynamic Kinetic Resolution for the Catalytic Asymmetric Total Synthesis of Antithrombotic Agents M58163 and M58169
Author(s) -
Saitoh Fumihiko,
Nishida Hidemitsu,
Mukaihira Takafumi,
Aikawa Kohsuke,
Mikami Koichi
Publication year - 2007
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.200600611
Subject(s) - kinetic resolution , chemistry , catalysis , pyrazine , lanthanum , diamine , total synthesis , enantioselective synthesis , combinatorial chemistry , antithrombotic , kinetic energy , resolution (logic) , stereochemistry , organic chemistry , medicine , physics , quantum mechanics , artificial intelligence , computer science , cardiology
Dynamic kinetic resolution is one of the most synthetically useful phenomena for asymmetric synthesis. Dynamic kinetic resolution for the catalytic asymmetric synthesis of a spiro[imidazo[1,2‐ a ]pyrazine‐2(3 H ),4′‐piperidin]‐5(1 H )‐one scaffold with a lanthanum‐linked BINOL complex is described. It is also clarified that starting materials, diamine 1 and keto ester 2 , play important roles not only as substrates but also as additives to modify an active species of the lanthanum complex. The catalytic asymmetric total syntheses of our antithrombotic agents M58163 and M58169 have thus been achieved via dynamic kinetic resolution.