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- Title
Synthesis of Enantiopure 1,5-Enynes and 1,5-Diynes with Propargylic Quaternary Centers.
- Authors
Pérez, Ignacio; Yuste, Francisco; Sánchez‐Obregón, Rubén; Toscano, Rubén A.; Alemán, José; Marzo, Leyre; Martín Castro, Ana M.; Alonso, Inés; García Ruano, José Luis
- Abstract
Diastereoselective quaternization of ortho-sulfinylbenzyl-methylpropargylic carbanions has been carried out with various allylic, propargylic, and benzylic halides. The stereoselectivity is efficiently controlled by the sulfinyl group, acting as a remote chiral auxiliary. Desulfinylation of the resulting compounds with tBuLi provides access to enantiopure 1,5-enynes, 1,5-diynes, and 4-arylalkynes bearing all-carbon quaternary propargylic centers.
- Subjects
ALKYNES; CHIRALITY; SULFOXIDES; ENYNES; CHEMICAL reactions
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 15, p3314
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500004