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Keywords:

  • aluminum acetals;
  • cognac lactone;
  • Oppenauer oxidation;
  • radical cyclization;
  • γ-lactone
Thumbnail image of graphical abstract

Cognac in the jar! An efficient one-pot sequence for the preparation of γ-lactones is described. Following reduction of α-bromo ester precursors with DIBAL-H and radical cyclization of the resulting O-aluminum acetals, a preparative in-situ Oppenauer-type oxidation of the cyclic O-aluminum acetal using simple aldehydes or ketones gives access to γ-lactones in high yields.

Featured Compounds

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  1. 1 - 23
Compound 1
Molecular Weight:451.352
Molecular Formula:C25H23BrO3
InChIKey:XQJJEGYCZAFRNI-UHFFFAOYSA-N
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Compound 3
Molecular Weight:514.6743
Molecular Formula:C33H43AlO3
InChIKey:ZUKQFXFKKPQAQW-BWIJTYSCSA-N
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Compound 4
Molecular Weight:374.4721
Molecular Formula:C25H26O3
InChIKey:MSNFHBKJYUTMFT-MLGOWYMSSA-N
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Compound 5
Molecular Weight:326.4933
Molecular Formula:C19H39AlO2
InChIKey:CTFGEBMTKSFRJQ-UHFFFAOYSA-N
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Compound 6
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:PHXATPHONSXBIL-UHFFFAOYSA-N
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Compound 7a
Molecular Weight:283.161
Molecular Formula:C13H15BrO2
InChIKey:AAZWKCLTAYBHBI-UHFFFAOYSA-N
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Compound 7b
Molecular Weight:297.188
Molecular Formula:C14H17BrO2
InChIKey:AQPRGXFRFKKEKV-UHFFFAOYSA-N
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Compound 7c
Molecular Weight:277.198
Molecular Formula:C12H21BrO2
InChIKey:QGKQVHBFDCJUST-FPLPWBNLSA-N
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Compound 7d
Molecular Weight:275.182
Molecular Formula:C12H19BrO2
InChIKey:BZYVBLJKIRFAJO-YRNVUSSQSA-N
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Compound 7e
Molecular Weight:329.186
Molecular Formula:C14H17BrO4
InChIKey:LAEQDPJQRNUWAS-UHFFFAOYSA-N
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Compound 7f
Molecular Weight:323.299
Molecular Formula:C12H23BrO3Si
InChIKey:YDUNWHYXAUIYFT-UHFFFAOYSA-N
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Compound 7g
Molecular Weight:451.352
Molecular Formula:C25H23BrO3
InChIKey:XQJJEGYCZAFRNI-UHFFFAOYSA-N
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Compound 8a
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:UMMZGLVGXQJFAR-CMPLNLGQSA-N
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Compound 8b
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:JALFREPJGKFMFE-XEEJXUNPSA-N
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Compound 8c
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:LNKSNVUONVLLFJ-UHFFFAOYSA-N
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Compound 8d
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:HSVGODOXADXSGZ-UHFFFAOYSA-N
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Compound 8e
Molecular Weight:250.2903
Molecular Formula:C14H18O4
InChIKey:ZHHZUONUOVMHJY-WCQYABFASA-N
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Compound 8f
Molecular Weight:244.4027
Molecular Formula:C12H24O3Si
InChIKey:MPHNXYYYBKNREK-VHSXEESVSA-N
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Compound 8g
Molecular Weight:372.4563
Molecular Formula:C25H24O3
InChIKey:LHVOHKXDSVCNRT-WMZHIEFXSA-N
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Compound 9
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:IWGYHTWXXHDZAY-UHFFFAOYSA-N
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Compound 10
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:VSMOENVRRABVKN-MRVPVSSYSA-N
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Compound 11
Molecular Weight:249.145
Molecular Formula:C10H17BrO2
InChIKey:BQHDGTPYIKHMFE-SECBINFHSA-N
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Compound 12
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:LOQFOBUZYRBURV-BDAKNGLRSA-N
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  1. 1 - 23