Beilstein J. Org. Chem.2013,9, 2688–2695, doi:10.3762/bjoc.9.305
starting materials. In this context, the recent introduction of difluoropropargyl bromide as fluorinated building block gave access to a wide variety of gem-difluoro-containing alkyne derivatives [21][22]. Recently, we have employed these fluorinated triple bond scaffolds in several types of cyclization
Beilstein J. Org. Chem.2010,6, No. 48, doi:10.3762/bjoc.6.48
; cycloisomerization; difluoropropargyl; enyne; ring-closing metathesis; Introduction
It has been estimated that as many as 25% of all synthetic pharmaceutical drugs contain an amide bond [1]. Commonly, β- and γ-lactams are present in many natural products and pharmaceuticals, and the introduction of a gem
fluorinated δ-lactams via cycloisomerization of gem-difluoropropargyl amides
Acknowledgements
We are grateful to the National Science Foundation for financial support (CHE-0809683) and to Professor Santos Fustero, Universidad de Valencia, Spain, for scientific cooperation and advice.
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Graphical Abstract
Scheme 1:
Diels–Alder reaction of diene 2 with 4 and 6. aThe other isomers of 7a and 7b were isolated in 8% a...