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Three-component reaction to synthesize E-vinyl silyl anti-1,2-diols via sequential [1,4]-O-to-O/[1,4]-C-to-O silyl migrations

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Abstract

A three-component reaction of geminal bis(silyl) allyl silyl ether, aldehyde and electrophile has been developed to synthesize trisubstituted E-vinyl silyl anti-1,2-diols. The approach features sequential [1,4]-O-to-O/[1,4]-C-to-O silyl migrations, which are triggered by the addition of the exo-oriented allyl anion to an aldehyde and terminated by the coupling of the resulting vinyl cuprate and electrophiles.

Graphical abstract: Three-component reaction to synthesize E-vinyl silyl anti-1,2-diols via sequential [1,4]-O-to-O/[1,4]-C-to-O silyl migrations

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Publication details

The article was received on 01 Apr 2018, accepted on 12 May 2018 and first published on 14 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00332G
Citation: Org. Chem. Front., 2018, Advance Article
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    Three-component reaction to synthesize E-vinyl silyl anti-1,2-diols via sequential [1,4]-O-to-O/[1,4]-C-to-O silyl migrations

    Q. Pu, X. Tang, L. Gao and Z. Song, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00332G

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