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One‐Pot High‐Yielding Synthesis of the DPP4‐Selective Inhibitor ABT‐341 by a Four‐Component Coupling Mediated by a Diphenylprolinol Silyl Ether
Author(s) -
Ishikawa Hayato,
Honma Masakazu,
Hayashi Yujiro
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201006204
Subject(s) - domino , nitro , aldol reaction , chemistry , silylation , isomerization , yield (engineering) , michael reaction , dream , amide , organic chemistry , stereochemistry , catalysis , psychology , materials science , alkyl , neuroscience , metallurgy
A dream come true : ABT‐341 was synthesized in high yield with excellent diastereo‐ and enantioselectivity in a one‐pot process mediated by a diphenylprolinol silyl ether (see scheme; TMS=trimethylsilyl). Thus, an asymmetric Michael reaction, a domino Michael/Horner–Wadsworth–Emmons reaction combined with a retro‐aldol reaction, base‐catalyzed isomerization, amide‐bond formation, and reduction of the nitro group all took place in a single flask.