One‐Pot High‐Yielding Synthesis of the DPP4‐Selective Inhibitor ABT‐341 by a Four‐Component Coupling Mediated by a Diphenylprolinol Silyl Ether | Zendy

Ishikawa Hayato | Zendy; Honma Masakazu | Zendy; Hayashi Yujiro | Zendy

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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.

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