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Samarium(II)-mediated 4-exo-trig cyclisations of unsaturated aldehydes. A stereoselective approach to functionalised cyclobutanols

Author(s): D. Johnston, C. F. McCusker, K. Muir, D. J. Procter

gamma,delta-Unsaturated aldehydes having a fully substituted centre in either the alpha- or beta-positions, have been prepared from substituted gamma-butyrolactones and undergo efficient 4-exo-trig cyclisation on treatment with samarium(II) iodide to give functionalised cyclobutanols. In all cases cyclisation occurs with complete diastereocontrol to give anti-cyclobutanol 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, alpha- 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.

Full version: Available here

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ISBN: 0300-922X
Publication Year: 2000
Periodical: Journal of the Chemical Society-Perkin Transactions 1
Periodical Number: 5
Pages: 681-695
Author Address: