Samarium-promoted cyclopropanation of allylic alcohols

Samarium-promoted cyclopropanation of allylic alcohols

The use of samarium/mercury amalgam in conjunction with diiodomethane or chloroiodomethane to generate samarium carbenoids for the efficient cyclopropanation of allylic alcohols is discussed. These hydroxyl-directed cyclopropanations occur under mild conditions and allow a wide range of substitution...

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Veröffentlicht in:Journal of organic chemistry 1989-07, Vol.54 (15), p.3525-3532
Hauptverfasser: Molander, Gary A, Harring, Lori S
Format: Artikel
Sprache:eng
Schlagworte:
400201 - Chemical & Physicochemical Properties
ALCOHOLS
ALKANES
Chemistry
CYCLOALKANES
DATA
DATA ANALYSIS
ELEMENTS
Exact sciences and technology
EXPERIMENTAL DATA
HYDROCARBONS
HYDROXY COMPOUNDS
INFORMATION
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
MEASURING INSTRUMENTS
MEASURING METHODS
MERCURY
METALS
NUMERICAL DATA
Organic chemistry
ORGANIC COMPOUNDS
RARE EARTHS
SAMARIUM
SYNTHESIS
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Zusammenfassung:The use of samarium/mercury amalgam in conjunction with diiodomethane or chloroiodomethane to generate samarium carbenoids for the efficient cyclopropanation of allylic alcohols is discussed. These hydroxyl-directed cyclopropanations occur under mild conditions and allow a wide range of substitution about both the olefin and the carbinol carbon in allylic alcohol substrates. High yields and high diastereoselectivities are observed for many substrates.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00276a008