Use of Pentamethyldisiloxane in the Palladium-Catalyzed Cyclization/Hydrosilylation of Functionalized Dienes

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 NaBAr4 [Ar = 3,5-C6H3(CF3)2] to form the corresponding silylated carbocycles in good yield...

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Published inOrganic letters Vol. 2; no. 10; pp. 1469 - 1471
Main Authors Pei, Tao, Widenhoefer, Ross A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.05.2000
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Drug Design
Indicators and Reagents
Molecular Conformation
Molecular Structure
Palladium
Physical Sciences
Science & Technology
Silanes - chemical synthesis
Silanes - chemistry
PHENYLDIMETHYLSILYL GROUP
OXIDATION
ORGANIC-SYNTHESIS
HYDROXYL GROUP
COMPLEX
SILAFUNCTIONAL COMPOUNDS
BOND
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ISSN1523-7060
1523-7052
DOI10.1021/ol005810u

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Summary: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 NaBAr4 [Ar = 3,5-C6H3(CF3)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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol005810u