Gold(I)-catalyzed rearrangement of propargylic alcohols to alpha,beta-unsaturated ketones

We have developed a gold(I)-catalyzed rearrangement of propargylic alcohols to a,alpha-beta-unsaturated ketones. The reaction might proceed through a dehydration of an alkynol, followed by an addition of water to a cumulene intermediate. The substituents of the alkynol play an important role in the...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 14; pp. 2107 - 2114
Main Authors Lee, Sang Ick, Back, Ji Young, Sim, So Hee, Chung, Young Keun
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.07.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
RING EXPANSION REACTION
CARBONYL-COMPOUNDS
UNMODIFIED ALDEHYDE
SELF-ALDOL CONDENSATION
gold
Meyer-Schuster
ALLYLIC ALCOHOLS
COMPLEX-CATALYZED ISOMERIZATION
alpha,beta-unsaturated ketones
CYCLOISOMERIZATION
ARYL IODIDES
propargylic alcohol
rearrangement
ENYNES
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Summary:We have developed a gold(I)-catalyzed rearrangement of propargylic alcohols to a,alpha-beta-unsaturated ketones. The reaction might proceed through a dehydration of an alkynol, followed by an addition of water to a cumulene intermediate. The substituents of the alkynol play an important role in the rearrangement.
ISSN:0039-7881
DOI:10.1055/s-2007-983725