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Reactions of Enone Ethylene Ketals with Methyl Diazomalonate/Bis(acetylacetonato)copper(II)
Author(s) -
Sezer özkan,
Daut Ayşe,
Anaç Olcay
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780811
Subject(s) - chemistry , cyclopropane , crotonaldehyde , ethylene , cinnamaldehyde , enone , yield (engineering) , medicinal chemistry , dimethyldioxirane , ketone , copper , organic chemistry , catalysis , stereochemistry , ring (chemistry) , materials science , metallurgy
Several cyclic and acyclic enones and their ethylene ketals/acetals were reacted with dimethyl diazomalonate under bis(acetylacetonato)copper(II) catalysis. Cyclohex‐2‐en‐1‐one ( 1 ) yielded only C–H insertion products 2 and 3 , whereas but‐3‐en‐2‐one gave a cyclopropane albeit in very low yield. The ethylene ketals 6 of cyclopent‐2‐en‐1‐one and cyclohex‐2‐en‐1‐one gave the corresponding cyclopropanes 7 , which were in turn cleaved to the ketones 8 . The acetals 9 and 10 of crotonaldehyde (( E )‐but‐2‐enal) and cinnamaldehyde (( E )‐3‐phenylprop‐2‐enal), respectively, yielded C–O insertion and [2,3]‐sigmatropic rearrangement products 11b, c and 12b, c , as well as cyclopropanes 11a and 11b , all of which are polyfunctional and synthetically useful compounds.