Hypervalent Iodine(III)‐Catalysed Enantioselective α‐Acetoxylation of Ketones

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 mCPBA in the presence of acetic...

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Bibliographic Details
Published in:Chemistry : a European journal 2020-08, Vol.26 (46), p.10417-10421
Main Authors: Hokamp, Tobias, Wirth, Thomas
Format: Article
Language:English
Subjects:
Acetic acid
Catalysis
Catalysts
Chemical synthesis
Chemistry
Communication
Communications
Enantiomers
Ethers
hypervalent iodine
Iodine
Ketones
Oxidation
Resorcinol
stereochemistry
α-acetoxylation
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Summary: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 mCPBA 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. An efficient and easy acetoxylation of ketones via their enolethers is described. With low catalyst loadings of a chiral aryliodine high stereoselectivities can be obtained under mild reaction conditions.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202000927