Nickel-catalyzed ring-opening hydroacylation of methylenecyclopropanes: Synthesis of γ,δ-unsaturated ketones from aldehydes

Journal of the American Chemical Society

Volumn 131, Issue 32, 2009, Pages 11298-11299

  Taniguchi, Hiroki ^a   Ohmura, Toshimichi ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALDEHYDES; C-C BONDS; CHEMICAL EQUATIONS; CYCLOPROPANE RING; DIASTEREOSELECTIVITIES; HIGH YIELD; HYDROACYLATION; IN-SITU; METHYLENECYCLOPROPANES; NICKEL CATALYST; RING OPENING; STEREOSPECIFIC; UNSATURATED KETONES;

CATALYSTS; CHEMICAL BONDS; CHEMICAL REACTIONS; KETONES; NICKEL; NICKEL ALLOYS; PROPANE;

ALDEHYDES;

ALDEHYDE DERIVATIVE; BENZALDEHYDE DERIVATIVE; CARBON; CYCLOPROPANE DERIVATIVE; KETONE DERIVATIVE; NICKEL;

ACYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DIASTEREOISOMER; MOLECULAR MECHANICS; RING OPENING; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 68849131552     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9046894     Document Type: Article

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30. GC/MS analysis indicated the formation of the dimer of 2a as a major byproduct. For the structure of the dimer, see the Supporting Information.
31. Isomerization of initially formed cis-3g to the trans isomer was observed in the reaction of 1g with 2a under these conditions.
32. Substituted MCPs such as benzylidenecyclopropane and (3- phenylpropylidene) cyclopropane did not give clean reactions. See the Supporting Information.
33. 1 with 2a gave deuterated 3b having a 1-deuterioethenyl group (99% D). For details, see the Supporting Information.