Premium
Vinyl Selenones Derived from d ‐Fructose: A New Platform for Fructochemistry
Author(s) -
Bhaumik Atanu,
Das Ashrukana,
Pathak Tanmaya
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600183
Subject(s) - chemistry , nucleophile , fructose , biomass (ecology) , combinatorial chemistry , organic chemistry , catalysis , oceanography , geology
d ‐Fructose, an inexpensive biomass precursor available on a large scale, has been used for the generation of enantiomerically pure chemical entities. Construction of vinyl selenone moieties on cyclic skeletons of d ‐fructose led to the highly reactive synthetic intermediates comprising of an electron‐deficient double bond along with an excellent leaving group. Reactions of these Michael acceptors with different nucleophiles afforded aziridines, thiiranes, cyclopropanes, dihydrofurans, dihydroisoxazole, dibenzyloxymethylfuran, and isonucleosides in moderate to good yields. This powerful and practical route provides a new platform for synthetic applications of renewable biomass precursors and adds to the toolbox for chemists interested in new chemical entities.