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Chiral Substituted 3‐Formylfurans from Carbohydrates: An Expedient Route via N ‐Bromosuccinimide (NBS)‐Mediated Electrophilic Cyclization
Author(s) -
Mal Kanchan,
Kaur Amanpreet,
Das Indrajit
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500272
Subject(s) - chemistry , n bromosuccinimide , electrophile , nucleophile , furan , pyran , enantioselective synthesis , combinatorial chemistry , derivative (finance) , heck reaction , total synthesis , stereochemistry , organic chemistry , halogenation , palladium , catalysis , financial economics , economics
Chiral, substituted 3‐formylfurans have found widespread applications as synthetic intermediates and are key structural motifs in a variety of bioactive natural products. However, methods for their preparation are scant. We report herein an efficient and general route to synthesize them from suitably protected 2‐iodoenones derived from glycals. The synthetic protocol involves Heck coupling between substituted 2‐iodoenones and olefins followed by N ‐bromosuccinimide (NBS)‐mediated electrophilic cyclization sequence, using H 2 O as a nucleophile. Similarly, a fully substituted chiral 3‐formylfuran can be prepared utilizing a two‐step approach starting with β ‐methylstyrene as an olefinic partner in the Heck coupling. Further, to demonstrate the potential of our method, we have synthesized a furo[3,2‐ c ]pyran derivative and a fully protected chiral furan.