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Molecules 2016, 21(6), 690; doi:10.3390/molecules21060690

Enantiopure Trisubstituted Tetrahydrofurans with Appendage Diversity: Vinyl Sulfone- and Vinyl Sulfoxide-Modified Furans Derived from Carbohydrates as Synthons for Diversity Oriented Synthesis

Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India
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Author to whom correspondence should be addressed.
Academic Editor: Andrea Trabocchi
Received: 19 March 2016 / Revised: 12 May 2016 / Accepted: 19 May 2016 / Published: 26 May 2016
(This article belongs to the Special Issue Diversity Oriented Synthesis 2016)
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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. View Full-Text
Keywords: vinyl sulfone; vinyl sulfoxide; modified tetrahydrofuran; Michael addition; diatereoselectivity vinyl sulfone; vinyl sulfoxide; modified tetrahydrofuran; Michael addition; diatereoselectivity
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Dey, D.; Pathak, T. Enantiopure Trisubstituted Tetrahydrofurans with Appendage Diversity: Vinyl Sulfone- and Vinyl Sulfoxide-Modified Furans Derived from Carbohydrates as Synthons for Diversity Oriented Synthesis. Molecules 2016, 21, 690.

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