title: Enantiopure Trisubstituted Tetrahydrofurans with Appendage Diversity: Vinyl Sulfone- and Vinyl Sulfoxide-Modified Furans Derived from Carbohydrates as Synthons for Diversity Oriented Synthesis.
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.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India. debanjanadey@gmail.com.
authors.forename: Debanjana
authors.initials: D
authors.lastname: Dey
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India. tpathak@chem.iitkgp.ernet.in.
authors.forename: Tanmaya
authors.initials: T
authors.lastname: Pathak
mesh_terms: D000588:Amines / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011143:Polyvinyl Chloride / Q000737:chemistry; D012451:Safrole / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry*; D013549:Sweetening Agents / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000588:Amines; D002241:Carbohydrates; D005663:Furans; D013450:Sulfones; D013549:Sweetening Agents; C009873:divinyl sulfone; D011143:Polyvinyl Chloride; D012451:Safrole; C005746:sulfoxide
keywords: Michael addition; diatereoselectivity; modified tetrahydrofuran; vinyl sulfone; vinyl sulfoxide