Hypervalent iodine(III)‐catalysed enantioselective α‐acetoxylation of ketones

Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 and Hokamp, Tobias 2020. Hypervalent iodine(III)‐catalysed enantioselective α‐acetoxylation of ketones. Chemistry - A European Journal 26 (46) , pp. 10417-10421. 10.1002/chem.202000927

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Abstract

An enantioselective catalytic synthesis of α‐acetoxylated ketones via 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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	0947-6539
Date of First Compliant Deposit:	16 April 2020
Date of Acceptance:	31 March 2020
Last Modified:	14 May 2023 23:29
URI:	https://orca.cardiff.ac.uk/id/eprint/131049

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