Gold-catalyzed deoxygenated cyclization of cis-2,4-dien-1-als with regioselective addition of two nucleophiles. One-pot synthesis of highly functionalized cyclopentene framework

Journal of the American Chemical Society

Volumn 129, Issue 13, 2007, Pages 3798-3799

  Lin, Chung Chang ^a   Teng, Tse Min ^a   Odedra, Arjan ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ALKADIENE; CYCLOPENTENE DERIVATIVE; GOLD;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 34247145512     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja069171f     Document Type: Article

References (25)

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20. The screening of these acid catalysts were performed with allylsilane and MeOH; the results were provided in Tables S1 and S2, respectively (see Supporting Information).
21. Table S3 shows additional products 32-38 given from the cyclization of these nucleophiles with aldehydes 1-3 and acyclic aldehyde s6.
22. 1H NOE, HMBC, and HMQC, respectively. These spectra are provided in Supporting Information.
23. 2 (0.01 M, 25°C, 6 h) provided oxacyclic compound 20 in 91% yield. This information suggests that formation of 20 is probably caused by rearrangement of kinetically favored product F according to the mechanism below. (Chemical Equation Presented)
24. The mechanistic discussion with the cyclization of aldehyde 2 with two allysilane molecules is provided in Supporting Information.
25. 3, which was shifted completely to δ 44.9 upon the addition of cis-dienal 3 (10 equiv); this information supports that this cationic gold species can bind to aldehyde to initiate the catalytic cyclization.