Abstract
Enantiomerically pure 2-substituted-2,5-dihydro-3-(aryl) sulfonyl/sulfinyl furans have been prepared from the easily accessible carbohydrate derivatives. The orientation of the substituents attached at the C-2 position of furans is sufficient to control the diastereoselectivity of the addition of various nucleophiles to the vinyl sulfone/sulfoxide-modified tetrahydrofurans, irrespective of the size of the group. The orientation of the substituents at the C-2 center also suppresses the influence of sulfoxides on the diastereoselectivity of the addition of various nucleophiles. The strategy leads to the creation of appendage diversity, affording a plethora of enantiomerically pure trisubstituted furanics for the first time.
Highlights
In order to increase the efficiency of a synthetic strategy for creating appendage, stereochemical, and scaffold diversities, explosive growth has taken place in the area of diversity-oriented synthesis (DOS) [1,2,3,4,5,6,7,8,9,10,11,12]
We developed a DOS-based strategy for the construction of enantiopure furofurans available carbohydrates, we developed a DOS-based strategy for the construction of enantiopure a program for the generation of enantiomerically pure non-carbohydrate chemicals from available from vinyl sulfone-modified mono- as well as bicylic-carbohydrates [21,22,23]
A simple strategy was devised for the synthesis of enantiomerically pure 2-substituted
Summary
In order to increase the efficiency of a synthetic strategy for creating appendage, stereochemical, and scaffold diversities, explosive growth has taken place in the area of diversity-oriented synthesis (DOS) [1,2,3,4,5,6,7,8,9,10,11,12]. It would be logical to use enantiopure substrates for the generation of new appendage or skeletal diversities with defined stereogenic centers in DOS, but in reality only a limited number of enantiopure “chiral pool” substrates such as carbohydrates have been utilized [2,3,7,8,13]. As a result of continued efforts, 2,5-dimethylfuran (DMF) [17], a molecule with the potential of an alternative fuel, is generated from the available biomass precursor D-fructose via 5-hydroxymethylfurfural (HMF). The conversion of biomass is not restricted to use as an alternative fuel alone. Recent research in this area is generating new tetrahydrofuran derivatives (furanics) such as 2,5-dimethyltetrahydrofuran (DMTHF), 2-methylfuran (2-MF), methyltetrahydrofuran (MTHF), 2-methylfurfural alcohol (MFA), 5-methyltetrahydrofurfural alcohol (MTHFA) etc.
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