Extending the scope of the Ferrier reaction: fragmentation-rearrangement reactions of selectively substituted 1,2-cyclopropanated glucose derivatives

Carbohydrate Research
Muganza MunyololoIlka Mohrholz

Abstract

Two further variations of the Ferrier-type allylic rearrangements of 1,2-cyclopropanated glucose derivatives bearing an acetoxylated carbon at the 1'-position are described. In the first, treatment of the cyclopropanated sugar with a nucleophile (ROH, PhSH, azide) and Lewis acid (BF(3)·Et(2)O or Al(OTf)(3)), gives 2-C-vinyl glucosides in good yields and α-selectivities. Alternatively, treatment with a combination of Lewis acid and acetic acid leads to a novel fragmentation-rearrangement to form a 2,3-dehydro-2-formyl-C-glycoside.

Citations

Mar 13, 2014·Carbohydrate Research·Supriya Dey, N Jayaraman
Jul 1, 2015·Beilstein Journal of Organic Chemistry·Henok H KinfeMokela S Sokamisa
Jan 18, 2014·Chemical Communications : Chem Comm·Patteti VenukumarPerali Ramu Sridhar
Feb 6, 2020·Organic Letters·Yasemin Mai-Linde, Torsten Linker

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