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Rhodium‐Catalyzed Regioselective 3‐Fluoroallylic Cyanation
Author(s) -
Middel Christoph,
Zygalski Lukas,
Meinecke Jannick,
Koert Ulrich
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001324
Subject(s) - regioselectivity , cyanation , chemistry , stereocenter , allylic rearrangement , substituent , rhodium , stereoselectivity , catalysis , selectivity , reagent , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , enantioselective synthesis
A rhodium catalyzed allylic cyanation of 3‐fluoroallylic trifluoroacetates with TMSCN and a bulky phosphite ligand gives 3‐fluoroallylic nitriles with a good substrate scope and high Z/E‐selectivity. For dialkylated substrates the fluorine substituent controls the regioselectivity in favor of the distal product. For the stereoselectivity of the allylic cyanation selected scalemic substrates showed inversion of the stereocenter and some or no stereoerosion.