Premium
A New Entry to the Stereoselective Introduction of an Ethynyl Group by a Radical Reaction: Synthesis of the Potential Antimetabolite 2′‐Deoxy‐2′‐ C ‐ethynyluridine
Author(s) -
Sukeda Makoto,
Ichikawa Satoshi,
Matsuda Akira,
Shuto Satoshi
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200290037
Subject(s) - stereoselectivity , yield (engineering) , radical cyclization , chemistry , fluoride , tetrabutylammonium fluoride , group (periodic table) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , physics , inorganic chemistry , thermodynamics
Atom‐transfer 5‐ exo cyclization and subsequent elimination occur when ethynyldimethylsilyl ethers of iodohydrins are treated with Et 3 B followed by tetrabutylammonium fluoride (TBAF) to give the corresponding cis ‐configured α‐hydroxy ethynyl compounds in high yield (see scheme). This is the first example of the use of a radical reaction to introduce an ethynyl group.