A sequential Claisen/ring-closing metathesis approach to the synthesis of spirocyclic cyclopentanes and cyclohexanes

Tetrahedron Letters

Volumn 44, Issue 49, 2003, Pages 8883-8885

  Beaulieu, Patrick ^a   Ogilvie, William W ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOPENTANE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CLAISEN CONDENSATION; IRELAND; NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0242361236     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.190     Document Type: Article

References (18)

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17. Metathesis of 9d was complete in less than 2 min at 0°C. Reaction at -78°C gave 64% conversion after 10 min with the same distribution of ring-opened products.
18. This was consistent with NMR observations on the subsequent metathesis product 10a . The proton α to the ester in the spectrum of the minor isomer shows couplings of 9.9 Hz and 5.4 Hz. The same hydrogen in the major product gives 6.6 and 6.8 Hz couplings. NOE measurements are consistent with this assignment.