Organoiodine‐Catalyzed Enantioselective Alkoxylation/Oxidative Rearrangement of Allylic Alcohols

An enantioselective catalytic alkoxylation/oxidative rearrangement of allylic alcohols has been established by using a Brønsted acid and chiral organoiodine. The presence of 20 mol % of an (S)‐proline‐derived C2‐symmetric chiral iodine led to enantioenriched α‐arylated β‐alkoxylated ketones in good...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-05, Vol.58 (22), p.7450-7453
Main Authors: Zhang, Dong‐Yang, Zhang, Ying, Wu, Hua, Gong, Liu‐Zhu
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
alkoxylation
asymmetric synthesis
Catalysis
Enantiomers
Iodine
Ketones
organocatalysis
Proline
rearrangements
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Summary:An enantioselective catalytic alkoxylation/oxidative rearrangement of allylic alcohols has been established by using a Brønsted acid and chiral organoiodine. The presence of 20 mol % of an (S)‐proline‐derived C2‐symmetric chiral iodine led to enantioenriched α‐arylated β‐alkoxylated ketones in good yields and with high levels of enantioselectivity (84–94 % ee). Shifting positions: Asymmetric catalytic alkoxylation/oxidative rearrangement of allylic alcohols was achieved by using a Brønsted acid and a chiral organoiodine. The reaction leads to optically active α‐arylated β‐etherized ketones in good yields and excellent stereoselectivity. Ts=4‐toluenesulfonyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201903007