Issue 5, 2000

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

Abstract

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 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, 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.

Supplementary files

Article information

Article type
Paper
Submitted
03 Dec 1999
Accepted
14 Jan 2000
First published
17 Feb 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 681-695

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

D. Johnston, C. F. McCusker, K. Muir and D. J. Procter, J. Chem. Soc., Perkin Trans. 1, 2000, 681 DOI: 10.1039/A909549G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements