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Volumn 12, Issue 20, 2010, Pages 4552-4555

Efficient catalytic, oxidative lactonization for the synthesis of benzodioxepinones using thiazolium-derived carbene catalysts

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; BENZOXEPIN DERIVATIVE; CARBENE; DRUG DERIVATIVE; LACTONE; METHANE; THIOL DERIVATIVE;

EID: 77957837046     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101854r     Document Type: Article
Times cited : (81)

References (70)
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    • Especially for the synthesis of macrolides, alternative methods targeting other positions to achieve ring closure, such as ring closing metathesis or (Suzuki) cross coupling, have gained in importance during the last years; for corresponding reviews, see, for RCM: Rouge dos Santos, A.; Kaiser, C. R.; Férézou, J.-P. Quim. Nova 2008, 31, 655
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    • For an NHC-catalyzed intramolecular hydroacylation yielding a phthalide scaffold, see
    • For an NHC-catalyzed intramolecular hydroacylation yielding a phthalide scaffold, see: Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4558
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    • Potential complications arise from overoxidation, especially in the case of electron-rich substrates and as well from missing selectivity if non- meso -diols are used. For a general review on oxidative esterifications, see
    • Potential complications arise from overoxidation, especially in the case of electron-rich substrates and as well from missing selectivity if non- meso -diols are used. For a general review on oxidative esterifications, see: Ekoue-Kove, K.; Wolf, C. Chem. - Eur. J. 2008, 14, 6302
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    • See also references cited in ref 14.
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    • In addition, benzimidazolium and N -Mes triazolium salts were evaluated, but provided much lower yields than 5d.
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    • We could observe a concentration effect: at 3 M, the ratio of 7A to 7B was determined to be ca. 9:1.
    • We could observe a concentration effect: at 3 M, the ratio of 7A to 7B was determined to be ca. 9:1.
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    • 2 (balloon) as terminal oxidant did not provide satisfactory yields (11 resp. 21%); however, for reports on strongly electron-deficient substrates that could be converted to their corresponding esters/acids without additional oxidant, see: Goswami, S.; Hazra, A. Chem. Lett. 2009, 38, 484
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    • For a recent application of NHC - Fe complexes for an aerobic esterification with boronic acids, see
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    • Initial attempts to apply this methodology to the synthesis of the most challenging eight-membered ring system (2a) affords the desired lactone in only 14% yield. However, this is remarkable as a related Ru-catalyzed approach only yielded 7% of the envisaged 8-ring. See ref 4h.
    • Initial attempts to apply this methodology to the synthesis of the most challenging eight-membered ring system (2a) affords the desired lactone in only 14% yield. However, this is remarkable as a related Ru-catalyzed approach only yielded 7% of the envisaged 8-ring. See ref 4h.


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