241473-85-8Relevant articles and documents
Samarium(ii)-mediated 4-exo-trig cyclisations of unsaturated aldehydes. a stereoselective approach to functionalised cyclobutanols
Johnston, Dcrek,McCusker, Catherine F.,Muir, Kenneth,Procter, David J.
, p. 681 - 695 (2007/10/03)
γ,δ-Unsaturated aldehydes having a fully substituted centre in either the α- or β-positions, have been prepared from substituted γ-butyrolactones and undergo efficient 4-exo-trig cyclisation on treatment with sarnarium(ii) iodide to give functionalised cyclobutanols. In all cases cyclisation occurs with complete diastereocontrol to give anti-cydobutanol products. The stereochemistry of the products has been confirmed by NOE and X-ray crystallographic studies. In the cyclisation of substrates having a third substituent on the double bond, α- to the ester, significant control is achieved at the third newly formed stereocentre lying outside the ring. The origin of the stereoselectivity at this third centre and its marked dependence on cosolvent are discussed. The Royal Society of Chemistry 2000.