Regioselective Pauson-Khand processes with olefins possessing extended phosphonates

Synlett

Volumn , Issue 4, 2010, Pages 649-653

  Kȩdzia, Jacek L ^a   Kerr, William J ^b   McPherson, Allan R ^b  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

functionalised phosphonates; Alkyne complexes; Annulations; Pauson Khand reaction; Regioselectivity

Indexed keywords

ALKENE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION;

EID: 77955345213     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219349     Document Type: Article

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40. 3): δ = 19.35 ppm. The ratio of 6e/7e in the unseparated mixture was calculated from the relative integral values of the proton NMR signals at δ = 7.30 ppm (6e) and 7.23 ppm (7e). All other regioisomeric ratios were established in a similar fashion. Isomer 7e was identified specifically as the 2,4-disubstituted cyclopentenone through the use of two-dimensional NMR experiments. Firstly, HSQC and HMBC techniques were used to determine the representative signals for the individual proton and carbon atoms. The regiochemistry of 7e was then determined by coupling correlations in the COSY spectrum and, specifically, with respect to the cyclopentenone C-4 methine proton showing direct coupling interactions with the C-3 olefinic proton, as well as the C-5 methylene unit and the O-methylene protons in the pendant side chain. The COSY spectrum for the 2,5-isomer 6e shows no coupling between the C-5 methine unit and the C-3 olefinic proton, whereas the same olefinic proton in this isomer does show a coupling interaction with the C-4 methylene unit. In all other cases (3, 4, 6a-d, 7a-d, 10, 11, 12, 13), the identity of the specific regioisomers was established more routinely through characteristic olefinic coupling patterns.