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Bimetallic Rhodium(II)/Indium(III) Relay Catalysis for Tandem Insertion/Asymmetric Claisen Rearrangement
Author(s) -
Chen Yushuang,
Dong Shunxi,
Xu Xi,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810410
Subject(s) - rhodium , bimetallic strip , catalysis , chemistry , claisen rearrangement , tandem , indium , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , composite material
Abstract The first example of catalytic insertion/asymmetric Claisen rearrangement tandem reaction of N ‐sulfonyl‐1,2,3‐triazoles with allyl alcohol esters was achieved by bimetallic relay catalytic systems involving achiral rhodium salt and chiral N , N ′‐dioxide–indium(III) complex. This manifold could overcome the limitation of single Rh II catalysis, providing a straight and facile route to various enantioenriched β/γ‐amino acid derivatives in high yields (up to 99 %) with excellent diastereo‐ and enantioselectivities (up to >95:5 dr, 98:2 er). Moreover, possible transition state models were proposed to elucidate the origin of chiral induction based on the control experiments and X‐ray crystal structure of the catalyst.