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

Molecules

Tanmaya Pathak¹  Debanjana Dey¹ 

[1] Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India;

关键词: vinyl sulfone;    vinyl sulfoxide;    modified tetrahydrofuran;    Michael addition;    diatereoselectivity;   

DOI  :  10.3390/molecules21060690

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown