O-Acetyl 1,3-Propanediol as an Acrolein Proelectrophile in Enantioselective Iridium-Catalyzed Carbonyl Allylation

O-Acetyl 1,3-propanediol serves as an acrolein proelectrophile in π-allyliridium-C,O-benzoate-catalyzed carbonyl allylations mediated by racemic α-substituted allylic acetates. Using the iridium catalyst modified by (R)-SEGPHOS, a variety of 3-hydroxy-1,5-hexadienes are formed with uniformly high le...

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Bibliographic Details
Published in:Organic letters 2023-05, Vol.25 (20), p.3659-3663
Main Authors: Verboom, Katherine L., Meyer, Cole C., Evarts, Madeline M., Jung, Woo-Ok, Krische, Michael J.
Format: Article
Language:English
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Summary:O-Acetyl 1,3-propanediol serves as an acrolein proelectrophile in π-allyliridium-C,O-benzoate-catalyzed carbonyl allylations mediated by racemic α-substituted allylic acetates. Using the iridium catalyst modified by (R)-SEGPHOS, a variety of 3-hydroxy-1,5-hexadienes are formed with uniformly high levels of regio-, anti-diastereo-, and enantioselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01022