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An efficient synthesis of highly optically active 4‐substituted‐2(5 H )‐furanones from chiral 3‐bromo‐2(5 H )‐furanone
Author(s) -
Fan XueE,
Huang Min,
Huang Hui,
Chen QingHua
Publication year - 2004
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20040221129
Subject(s) - chemistry , optically active , absolute configuration , pyrimidine , proton nmr , stereochemistry , base (topology) , tandem , medicinal chemistry , organic chemistry , mathematical analysis , materials science , mathematics , composite material
Highly optically active 4‐substituted‐2(5 H )‐furanones 6a‐6j were obtained in good yields with de ⩾98% by the tandem Michael addition/elimination reaction of chiral 3‐bromo‐2(5 H )‐furanone (4a), which was conveniently prepared starting from 2‐furaldehyde under mild conditions. The products were identified on the basis of their satisfactory elemental analysis and spectroscopic data of IR, W, 1 H NMR, 13 C NMR and mass spectra. The stereochemistry and absolute configuration of this type of compounds were established by the X‐ray crystallographic study. The reaction provided a short and efficient synthesis of the interesting highly optically active 4‐substituted‐2(5 H )‐furanones containing an active pyrimidine and a purine base group.