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HERO ID
4082075
Reference Type
Journal Article
Title
LANTHANIDE TRIFLATES AS WATER-TOLERANT LEWIS-ACIDS - ACTIVATION OF COMMERCIAL FORMALDEHYDE SOLUTION AND USE IN THE ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES IN AQUEOUS-MEDIA
Author(s)
Kobayashi, S; Hachiya, I
Year
1994
Is Peer Reviewed?
Yes
Journal
Journal of Organic Chemistry
ISSN:
0022-3263
EISSN:
1520-6904
Volume
59
Issue
13
Page Numbers
3590-3596
DOI
10.1021/jo00092a017
Web of Science Id
WOS:A1994NV24000017
URL
https://www.scopus.com/inward/record.uri?eid=2-s2.0-33751157649&doi=10.1021%2fjo00092a017&partnerID=40&md5=81886fbd3e496530d0bbd3167a202707
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Abstract
Lanthanide trifluoromethanesulfonates (triflates), especially ytterbium triflate (Yb(OTf)(3)), were found to be stable Lewis acids in water. In the presence of a catalytic amount of lanthanide triflate, formaldehyde in water solution (commercial formaldehyde solution) was activated and the hydroxymethylation reaction of silyl enol ethers proceeded smoothly. Lanthanide triflates were also quite effective in the aldol reaction of silyl enol ethers with aldehydes in aqueous media, and water-soluble aldehydes such as acetaldehyde, acrolein, and chloroacetaldehyde could be employed for direct use. Moreover, in all these reactions, lanthanide triflates were quantitatively recovered after the reactions were completed and could be reused.
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