Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones

dc.contributor.author	Salin A.
dc.contributor.author	Islamov D.
dc.date.accessioned	2020-01-15T21:47:46Z
dc.date.available	2020-01-15T21:47:46Z
dc.date.issued	2019
dc.identifier.issn	1477-0520
dc.identifier.uri	https://dspace.kpfu.ru/xmlui/handle/net/156003
dc.description.abstract	© 2019 The Royal Society of Chemistry. The highly efficient addition of phosphorus and carbon pronucleophiles to α-methylene-γ-butyrolactones (tulipalin A and arglabin) under n-Bu3P catalysis is reported. Kinetic experiments indicate that the unprecedentedly high reactivity of α-methylene-γ-butyrolactones results from the rigid s-cis geometry of the 1-oxa-1,3-butadiene moiety that favors generation of zwitterionic intermediate stabilized by interaction between the phosphonium center and adjacent carbonyl oxygen. The presented strategy offers an economical and practical method for functionalization of natural biologically active α-methylene-γ-butyrolactones with high levels of chemo- and stereoselectivity.
dc.relation.ispartofseries	Organic and Biomolecular Chemistry
dc.title	Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones
dc.type	Article
dc.relation.ispartofseries-issue	31
dc.relation.ispartofseries-volume	17
dc.collection	Публикации сотрудников КФУ
dc.relation.startpage	7293
dc.source.id	SCOPUS14770520-2019-17-31-SID85070461946

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