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Cross‐Metathesis/Isomerization/Allylboration Sequence for a Diastereoselective Synthesis of Anti ‐Homoallylic Alcohols from Allylbenzene Derivatives and Aldehydes
Author(s) -
Hemelaere Rémy,
Carreaux François,
Carboni Bertrand
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403954
Subject(s) - isomerization , chemistry , metathesis , sequence (biology) , enantioselective synthesis , ruthenium , salt metathesis reaction , combinatorial chemistry , catalysis , iridium , organic chemistry , polymerization , biochemistry , polymer
We describe a highly diastereoselective approach to anti ‐homoallylic alcohols from allylbenzene derivatives and aldehydes. The strategy is based on a cross‐metathesis/isomerization/allylboration sequence catalyzed successively by ruthenium and iridium. This methodology provides another way to access this class of compounds, which leads to the preparation of hitherto‐unknown homoallylic alcohols without the requirement to control the stereochemistry of the 1‐alkenyl boronate intermediates. Our study towards an enantioselective version of this sequential reaction is also reported.