Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α‑Carbonyl Sulfoxonium Ylides

Enantioselective cyclopropanation of α-carbonyl sulfoxonium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular cyclopropanation of SY in the presence of a chiral diene in up to 96% yield and 98% enan...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 46; pp. 8503 - 8508
Main Authors Vidal, Lucas, Chen, Pan-Pan, Nicolas, Eva, Hackett, Andrew, Robertson, Craig M., Houk, Kendall N., Aïssa, Christophe
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.11.2022
Amer Chemical Soc
Subjects
Alkenes
Catalysis
Chemistry
Chemistry, Organic
Iridium
Letter
Physical Sciences
Science & Technology
Stereoisomerism
CARBENE PRECURSORS
DIAZOACETATES
CRYSTAL-STRUCTURES
INSERTION
BOND
COMPLEXES
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Summary:Enantioselective cyclopropanation of α-carbonyl sulfoxonium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular cyclopropanation of SY in the presence of a chiral diene in up to 96% yield and 98% enantioselectivity. Moreover, density functional theory calculations suggest that the re face of the olefin preferably attacks an iridium carbene intermediate in an asynchronous concerted step that is independent of the geometry of the olefin.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03396