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Enantioselective Synthesis of the Spirotropanyl Oxindole Scaffold through Bimetallic Relay Catalysis
Author(s) -
Jia ZhiJun,
Shan Gang,
Daniliuc Constantin G.,
Antonchick Andrey P.,
Waldmann Herbert
Publication year - 2018
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.201712882
Subject(s) - oxindole , enantioselective synthesis , catalysis , bimetallic strip , diazo , chemistry , intramolecular force , combinatorial chemistry , intermolecular force , cycloaddition , stereochemistry , organic chemistry , molecule
Spirotropanyl oxindole alkaloids like alstonisine and chitosenine show a wide range of bioactivites. We report the first enantioselective synthesis of the spirotropanyl oxindole scaffold by means of a bimetallic relay catalysis strategy. A new class of E ‐oximino α‐diazo ketones was developed for the intramolecular generation of transient azomethine ylides catalyzed by an achiral Rh II complex and a subsequent intermolecular 1,3‐dipolar cycloaddition catalyzed by a chiral N , N′ ‐dioxide Nd III Lewis acid complex. The enantioselectively catalyzed transformation has broad scope and yields the desired spirotropanyl oxindole cycloadducts in high yields and with very high enantio‐ and diastereoselectivity.