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Samarium Diiodide Mediated Coupling of 2‐Pyridylsulfonyl Furanosides with Aldehydes and Ketones: A General Synthesis of C ‐Furanosides
Author(s) -
Wang Jin,
Gasc Fabien,
Prandi Jacques
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403640
Subject(s) - chemistry , anomer , stereochemistry , substituent , diethylzinc , organic chemistry , enantioselective synthesis , catalysis
Abstract Diiodosamarium‐mediated coupling of anomeric 2‐pyridyl sulfones derived from furanosides with carbonyl compounds, aldehydes, and ketones gave α‐hydroxylated 2,5‐ trans ‐dialkylated tetrahydrofurans with good yields and useful stereoselectivities. The main control element of the reaction is the substituent on the 4‐position or the starting furanosyl sulfone. C ‐Furanosides of D ‐arabinose and of D ‐ribose were obtained from sulfones prepared from the corresponding furanosides. Finally, a di‐ C ‐arabinofuranoside, a C ‐disaccharide analogue of a major motif of the arabinogalactan from the mycobacterial cell wall, was prepared.