Use of pentamethyldisiloxane in the palladium-catalyzed cyclization/hydrosilylation of functionalized dienes.
[reaction--see text] Pentamethyldisiloxane reacts with a range of functionalized dienes in the presence of a catalytic 1:1 mixture of (N-N)Pd(Me)Cl [N-N = 1, 10-phenanthroline or (R)-(+)-4-isopropyl-2-(2-pyridinyl)-2-oxazoline] and NaBAr(4) [Ar = 3,5-C(6)H(3)(CF(3))(2)] to form the corresponding silylated carbocycles in good yield and with good stereoselectivity. Treatment of these silylated carbocycles with excess KF and peracetic acid at room temperature for 48 h formed the corresponding alcohols in excellent yield with retention of stereochemistry.
Pei
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Duke University, P. M. Gross Chemical Laboratory, Durham, North Carolina 27708-0346, USA.
Widenhoefer
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D002384:Catalysis; D003500:Cyclization; D015195:Drug Design; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D010165:Palladium; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D012821:Silanes; C410412:pentamethyldisiloxane; D010165:Palladium