Issue 40, 2016

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
02 Aug 2016
Accepted
15 Sep 2016
First published
20 Sep 2016
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2016,14, 9554-9559

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

A. Throup, L. H. Patterson and H. M. Sheldrake, Org. Biomol. Chem., 2016, 14, 9554 DOI: 10.1039/C6OB01661H

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