The semi-pinacol rearrangement of homochiral epoxyalcohols catalysed by rare earth triflates

alpha,beta -Epoxy ketones, prepared using the polyleucine catalysed asymmetric epoxidation of enones, can be converted into alpha -substituted beta -hydroxy ketones via carbonyl alkylation with Grignard reagents followed by ytterbium triflate catalysed semi-pinacol rearrangement of the resulting epo...

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Bibliographic Details
Published inPerkin 1 : an international journal of organic and bio-organic chemistry no. 11; pp. 1253 - 1255
Main Authors Bickley, JF, Hauer, B, Pena, PCA, Roberts, SM, Skidmore, J
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EPOXIDES
KETONES
ACID
STEREOSELECTIVE CONSTRUCTION
CARBONYL-COMPOUNDS
CENTERS
SILYL ETHER REARRANGEMENTS
EPOXIDATION
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Summary:alpha,beta -Epoxy ketones, prepared using the polyleucine catalysed asymmetric epoxidation of enones, can be converted into alpha -substituted beta -hydroxy ketones via carbonyl alkylation with Grignard reagents followed by ytterbium triflate catalysed semi-pinacol rearrangement of the resulting epoxyalcohols.
ISSN:1472-7781
DOI:10.1039/b101838h