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Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system

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Abstract

The first example of asymmetric 1,3-dipolar cycloadditions between diazo imine-derived cyclic azomethine ylides and acryloylpyrazolidinone using a rhodium(II) complex/chiral Lewis acid binary system is reported. The asymmetric cycloadditions afforded optically active 8-oxabicyclo[3.2.1]octanes with high diastereo- and enantioselectivities (up to >99 : 1 dr, 99% ee). A switch of exo/endo-selectivity was observed depending on the diazo substrates.

Graphical abstract: Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system

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Publication details

The article was received on 22 Nov 2018, accepted on 12 Dec 2018 and first published on 18 Dec 2018


Article type: Communication
DOI: 10.1039/C8CC09224A
Citation: Chem. Commun., 2019, Advance Article
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    Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system

    H. Suga, M. Yoshiwara, T. Yamaguchi, T. Bando, M. Taguchi, A. Inaba, Y. Goto, A. Kikuchi, K. Itoh and Y. Toda, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC09224A

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