Use of pentamethyldisiloxane in the palladium-catalyzed cyclization/ hydrosilylation of functionalized dienes

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1469-1471

  Pei, Tao ^a   Widenhoefer, Ross A ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PALLADIUM; PENTAMETHYLDISILOXANE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; DRUG DESIGN; SYNTHESIS;

CATALYSIS; CYCLIZATION; DRUG DESIGN; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PALLADIUM; SILANES;

EID: 0034682139     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005810u     Document Type: Article

References (20)

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16. Available from Gelest, Inc. (Tullytown, PA) for ca. $ 1/g.
17. 3b
18. General procedure for cyclization/hydrosilylation: the diene (5.0 mmol) and pentamethyldisiloxane (2.15 g, 15.0 mmol) were added sequentially to a solution of 2a (84 mg, 0.25 mmol) and 2c (259 mg, 0.25 mmol) in DCE (50 mL) at 0 °C. The resulting pale yellow solution was stirred for either 10 inin at 0 °C (Table 1, entries 1-6, 13) or at room temperature for 1-12 h (Table 1, entries 7-12) to form a dark brown solution. Solvent and excess silane were evaporated under vacuum, and the brown residue was dissolved in hexane/EtOAc (24:1) and filtered through a plug of silica gel. Concentration under vacuum gave the corresponding silylated carbocycle as a colorless to pale yellow oil in 80-99% purity which was oxidized without further purification. Although carbocycle 3 decomposed slightly upon silica gel chromatography, all other silylated carbocycles displayed no significant sensitivity toward silica gel.
19. 4), concentrated, and chromatographed on silica gel to give the pure alcohol as a colorless oil.
20. 3 (89% ee).