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 | Zendy

Sukeda Makoto | Zendy; Ichikawa Satoshi | Zendy; Matsuda Akira | Zendy; Shuto Satoshi | Zendy

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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.

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