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Synergistic silver/scandium catalytic spiroketalization of β-alkynyl ketones for the atom economical synthesis of skeletally diverse spirocyclic isochromenes

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Abstract

Two types of new synergistic silver/scandium catalytic spiroketalizations of β-alkynyl ketones have been achieved, delivering a variety of skeletally diverse spirocyclic isochromenes in generally good yields and good diastereoselectivity in an atom economical manner. In the former, bimetallic catalytic [4 + 2] cycloaddition worked well to provide a series of 6,6-benzannulated spiroketals, whereas the latter gave unprecedented nitrogen-containing 5,6-benzannulated spiroketals through catalytic [3 + 2] cycloaddition under mild conditions.

Graphical abstract: Synergistic silver/scandium catalytic spiroketalization of β-alkynyl ketones for the atom economical synthesis of skeletally diverse spirocyclic isochromenes

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Publication details

The article was received on 24 Nov 2018, accepted on 03 Jan 2019 and first published on 03 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01277F
Citation: Org. Chem. Front., 2019, Advance Article
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    Synergistic silver/scandium catalytic spiroketalization of β-alkynyl ketones for the atom economical synthesis of skeletally diverse spirocyclic isochromenes

    C. Ji, Y. Pan, F. Geng, W. Hao, S. Tu and B. Jiang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01277F

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