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Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents
Author(s) -
Malmedy Florence,
Wirth Thomas
Publication year - 2016
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.201603022
Subject(s) - hypervalent molecule , stereoselectivity , iodine , reagent , chemistry , ketone , ibuprofen , organic chemistry , combinatorial chemistry , catalysis , medicine , pharmacology
Abstract The first stereoselective version of an iodine(III)‐mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α‐arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid‐based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.