TY - JOUR
T1 - One-pot high-yielding synthesis of the DPP4-selective inhibitor ABT-341 by a four-component coupling mediated by a diphenylprolinol silyl ether
AU - Ishikawa, Hayato
AU - Honma, Masakazu
AU - Hayashi, Yujiro
PY - 2011/3/14
Y1 - 2011/3/14
N2 - 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.
AB - 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.
KW - Michael addition
KW - asymmetric synthesis
KW - domino reactions
KW - multicomponent reactions
KW - organocatalysis
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U2 - 10.1002/anie.201006204
DO - 10.1002/anie.201006204
M3 - Article
AN - SCOPUS:79952503331
SN - 1433-7851
VL - 50
SP - 2824
EP - 2827
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 12
ER -