Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones

Description

Yes / Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing δ lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity. / The work was funded by Yorkshire Cancer Research

Links & Downloads

1. Throup A, Patterson LH and Sheldrake HM (2016) Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicylolactones. Organic and Biomolecular Chemistry. 40(14): 9554-9559.
2. http://hdl.handle.net/10454/9488
3. https://doi.org/10.1039/C6OB01661H

Tags

Cyclobutanes

Thermal enamine

Lactone

Lactam

Cyclobutenes

Additional Fields

Identifer	oai:union.ndltd.org:BRADFORD/oai:bradscholars.brad.ac.uk:10454/9488
Date	20 September 2016
Creators	Throup, Adam E., Patterson, Laurence H., Sheldrake, Helen M.
Source Sets	Bradford Scholars
Language	English
Detected Language	English
Type	Article, Published version
Rights	© 2016 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence., CC-BY