Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones. Issue 40 (20th September 2016)

• Record Type: Journal Article
• Authors: Throup, Adam; Patterson, Laurence H.; Sheldrake, Helen M.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 40(2016)
• Page Start: 9554
• Page End: 9559
• Publication Date: 2016-09-20
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01661h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A new method for the synthesis of highly functionalised cyclobutenes. 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.