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Organocatalytic Michael Addition of Malonates to Isatylidene‐3‐acetaldehydes: Application to the Total Synthesis of (−)‐Debromoflustramine E
Author(s) -
Liu Renrong,
Zhang Junliang
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300977
Subject(s) - total synthesis , enantioselective synthesis , oxindole , michael reaction , conjugate , yield (engineering) , chemistry , organic chemistry , stereochemistry , mathematics , catalysis , materials science , mathematical analysis , metallurgy
Flustering oxindoles : An enantioselective synthesis of 3,3′‐disubstituted oxindoles by conjugate addition of malonates to isatylidene‐3‐acetaldehydes in high yield and enantioselectivity is developed (see scheme). The synthetic utility of this reaction is demonstrated by the synthesis of three oxindole core structures and the asymmetric total synthesis of debromoflustramine E.