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Volumn 47, Issue 27, 2008, Pages 5063-5066

PtII-catalyzed synthesis of 9-oxabicyclo[3.3.1]nona-2,6-dienes from 2-alkynyl-1-carbonylbenzenes and allylsilanes by an allylation/annulation cascade

Author keywords

Allylation; Annulation; Oxygen heterocycles; Platinum

Indexed keywords

ACETYLENE; CHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

EID: 49849093426     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800826     Document Type: Article
Times cited : (74)

References (39)
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    • 3AuOTf] gave desired oxatricyclic species 3 in a 25% yield.
    • 3AuOTf] gave desired oxatricyclic species 3 in a 25% yield.
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    • 1H NOE spectra of key compounds are provided in the Supporting Information.
    • 1H NOE spectra of key compounds are provided in the Supporting Information.
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    • 2/CO-catalyzed cyclization of 4c with 1-methylstyrene in hot toluene. See the leading paper: N. Asao, T. Kasahara, Y. Yamamoto, Angew. Chem. 2003, 115, 3628;
    • 2/CO-catalyzed cyclization of 4c with 1-methylstyrene in hot toluene. See the leading paper: N. Asao, T. Kasahara, Y. Yamamoto, Angew. Chem. 2003, 115, 3628;
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    • For the mechanism of formation of chrysene 7, see A. Das, H.-H. Liao R.-S. Liu, J. Org. Chem. 2007, 72, 9214.
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    • For formation of 1H-isochromenes from hydroalkoxylation of alkyne, see reference [5e] and selected examples: a X. Yao, C.-J. Li, Org. Lett. 2006, 8, 1953;
    • For formation of 1H-isochromenes from hydroalkoxylation of alkyne, see reference [5e] and selected examples: a) X. Yao, C.-J. Li, Org. Lett. 2006, 8, 1953;
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    • The calculations were done with Gaussian-98 package at level B3LYP/6-31 + G*; details are provided in the Supporting information.
    • The calculations were done with Gaussian-98 package at level B3LYP/6-31 + G*; details are provided in the Supporting information.
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    • For metal-catalyzed addition of a tethered phenol or enol to an enol ether of 1H-isochromenes, see: A. Beeler, S. Su, C. A. Singleton, J. A. Proco, Jr., J. Am. Chem. Soc. 2007, 129, 1413.
    • For metal-catalyzed addition of a tethered phenol or enol to an enol ether of 1H-isochromenes, see: A. Beeler, S. Su, C. A. Singleton, J. A. Proco, Jr., J. Am. Chem. Soc. 2007, 129, 1413.
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    • Ketones are generally inactive toward metal-catalyzed allylation reactions.[1] The high yields of oxatricyclic products 5a-5d may arise from addition of allylsilane to benzopyrilium species C, 11] rather than by the mechanism proposed in Scheme 2. We thank one reviewer for this valuable comment
    • [11] rather than by the mechanism proposed in Scheme 2. We thank one reviewer for this valuable comment.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.