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Hypervalent Iodine(III)‐Catalysed Enantioselective α‐Acetoxylation of Ketones
Author(s) -
Hokamp Tobias,
Wirth Thomas
Publication year - 2020
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.202000927
Subject(s) - enantioselective synthesis , hypervalent molecule , resorcinol , catalysis , chemistry , iodine , enol , acetic acid , organic chemistry , medicinal chemistry
An enantioselective catalytic synthesis of α‐acetoxylated ketones through I(I)/I(III) catalysis using a resorcinol/lactamide‐based chiral iodoarene is reported. Catalyst turnover by in situ generation of the active iodine(III) derivative is achieved by oxidation with m CPBA in the presence of acetic acid. The prior transformation of ketones to easily accessible acetyl enol ethers is beneficial and yields up to 97 % with enantioselectivities up to 88 % ee are obtained using only low catalyst loadings of only 5 mol % under mild reaction conditions.