Dey, Debanjana ; Pathak, Tanmaya (2016) Enantiopure trisubstituted tetrahydrofurans with appendage diversity: vinyl sulfone- and vinyl sulfoxide-modified furans derived from carbohydrates as synthons for diversity oriented synthesis Molecules, 21 (6). Article ID 690, 18 pages. ISSN 1420-3049
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Official URL: http://www.mdpi.com/1420-3049/21/6/690
Related URL: http://dx.doi.org/10.3390/molecules21060690
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.
Item Type: | Article |
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Source: | Copyright of this article belongs to Molecular Diversity Preservation International (MDPI). |
Keywords: | Vinyl Sulfone; Vinyl Sulfoxide; Modified Tetrahydrofuran; Michael Addition; Diatereoselectivity |
ID Code: | 103706 |
Deposited On: | 22 Mar 2017 05:50 |
Last Modified: | 22 Mar 2017 05:51 |
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