Issue 13, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
01 Apr 2018
Accepted
12 May 2018
First published
14 May 2018

Org. Chem. Front., 2018,5, 2035-2039

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, 5, 2035 DOI: 10.1039/C8QO00332G

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