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Iridium‐Catalyzed 1,3‐Hydrogen Shift/Chlorination of Allylic Alcohols
Author(s) -
Ahlsten Nanna,
Bermejo Gómez Antonio,
MartínMatute Belén
Publication year - 2013
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.201301013
Subject(s) - allylic rearrangement , chemistry , regioselectivity , steric effects , electrophile , halogenation , isomerization , ketone , catalysis , organic synthesis , acetophenone , lewis acids and bases , organic chemistry , combinatorial chemistry , medicinal chemistry
Tandem : Allylic alcohols react with N ‐chlorosuccinimide (NCS) in a tandem 1,3‐H shift/CCl bond formation leading to α‐chloroketones and α‐chloroaldehydes. The reactions proceed with complete selectivity to give single constitutional isomers of monochlorinated carbonyl compounds. The utility of the transformation is illustrated by the straightforward synthesis of 4,5‐disubstituted 2‐aminothiazoles from allylic alcohols.