Divergent amine-catalyzed [2+2] annulation of allenoates with azodicarboxylates: facile synthesis of 1, 2-diazetidines. Issue 46 (18th November 2015)

• Record Type: Journal Article
• Authors: Xu, Silong; Chen, Jingrong; Shang, Jian; Qing, Ziqi; Zhang, Junjie; Tang, Yuhai
• Is Part Of: Tetrahedron letters. Volume 56:Issue 46(2015)
• Page Start: 6456
• Page End: 6459
• Publication Date: 2015-11-18
• Subjects: ASFIGHVBQPNJEV-VBKFSLOCSA-N -- JBCBDXGJESMXQB-XFFZJAGNSA-N -- QZDMNHCIZOPOIX-CLFYSBASSA-N -- CLICLACTRIASOU-LUAWRHEFSA-N -- ZVJWIAIOEIDWSN-WQLSENKSSA-N -- BMKGAPZTJZGHLM-NTMALXAHSA-N -- YNCZCKRZPLUALP-LCYFTJDESA-N -- LXMYRFGUBBJUKK-LUAWRHEFSA-N -- ZSYGCVJNDFFLGG-AQTBWJFISA-N -- VQCRNWKIKFPNAX-SSZFMOIBSA-N -- GQJAAMLFWWACNX-UHFFFAOYSA-N -- GAVQZZDPPRAVIV-GHRIWEEISA-N -- GCOAYIQDUSPLRE-FYWRMAATSA-N -- GAVQZZDPPRAVIV-LGMDPLHJSA-N -- GCOAYIQDUSPLRE-SQFISAMPSA-N -- VRBLMPYCGVUKOH-YBEGLDIGSA-N -- UDBOMGHPUVWNHK-UVTDQMKNSA-N; Lewis base catalysis -- Allenoates -- [2+2] annulations -- Diazetidines -- Azodicarboxylates; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.151
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: A divergent DABCO-catalyzed [2+2] annulation reaction of allenoates with azodicarboxylates is developed for an easy synthesis of 3-alkylidene-1, 2-diazetidines. Abstract: In this Letter, we described a distinct DABCO-catalyzed [2+2] annulation reaction of allenoates with azodicarboxylates which affords 3-alkylidene-1, 2-diazetidines in moderate yields with excellent stereo- and regioselectivity. This reaction constitutes the first example of Lewis base-catalyzed annulation of allenoates with azodicarboxylates, and showcases a divergent reactivity between phosphines and amines.