Iodotrimethylsilane-promoted 1,4-addition of alkynylcopper reagents to {alpha}, {beta}-unsaturated ketones and aldehydes

Conference · Sun Dec 31 00:00:00 EST 1995

OSTI ID:250126

Eriksson, M; Iliefski, T; Nilsson, M; Olsson, T ^[1]

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1. Chalmers Univ. of Technology, Goeteborg (Sweden)

In the presence of TMSI copper acetylides react with cyclic {alpha},{beta}-enones, some s-trans enones and also to {alpha},{beta}-unsaturated aldehydes to give {gamma},{delta}-acetylenic ketones via the silyl enol ethers. Conjugate addition of alkyl and alkenyl copper reagents is a very useful method for the formation of carbon-carbon bonds. However, the conjugate addition of alkynyl copper compounds has so far remained a difficult task. Other methods based on organometallic reagents derived from aluminium, boron, and zinc have been reported. This is the first example of conjugate addition with copper acetylides to {alpha},{beta}-unsaturated carbonyl compounds.

• OSTI ID: 250126
• Report Number(s): CONF-9508100-; TRN: 96:002623-0064
• Resource Relation: Conference: 8. IUPAC symposium on organometallic chemistry directed towards organic synthesis, Santa Barbara, CA (United States), 6-10 Aug 1995; Other Information: PBD: 1995; Related Information: Is Part Of Eight IUPAC symposium on organometallic chemistry directed towards organic synthesis (OMCOS 8); PB: 375 p.
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
KETONES
CHEMICAL REACTIONS
ALDEHYDES
ORGANOMETALLIC COMPOUNDS
COPPER COMPLEXES