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Übergangsmetall‐katalysierte Reaktionen von ungesättigten α‐Diazo‐α‐(trimethylsilyl)essigestern mit Carbonylverbindungen
Author(s) -
Alt Mechthild,
Maas Gerhard
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270831
Subject(s) - chemistry , allylic rearrangement , enol ether , trimethylsilyl , diazo , benzaldehyde , enol , medicinal chemistry , ketone , catalysis , organic chemistry , acetone , ether , trifluoromethanesulfonate , acetal
Transition Metal Catalyzed Reactions of Unsaturated α‐Diazo‐α‐(trimethylsilyl)acetates with Carbonyl Compounds Some reactions of unsaturated α‐diazo‐α‐(trimethylsilyl)acetates with aldehydes or acetone under the catalytic action of rhodium(II) perfluorobutyrate or copper(I) triflate have been investigated. Thus, the allylic ester 6a affords 1,3‐dioxolan‐4‐ones 8 under Rh(II) catalysis; the Cu‐catalyzed reaction yields 8 , oxirane 9 , and the 3‐oxabicyclo[3.1.0]hexane 10 . The propargylic ester 6b does not react in a clear fashion with benzaldehyde, 1,3‐Dioxolanes result from the homoallylic ester 6c and aldehydes, but enol ether 14 from 6c and acetone.