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- Title
Straightforward and Highly Stereoselective Synthesis of 3,3,4-Trifluoropyrrolidines Involving 1,3-Dipolar Cycloaddition with 2,3,3-Trifluoroacrylate.
- Authors
Yamada, Shigeyuki; Higashi, Masao; Konno, Tsutomu; Ishihara, Takashi
- Abstract
The reactions of benzyl 2,3,3-trifluoroacrylate with azomethine ylides, generated by the treatment of imino esters with lithium diisopropylamide, took place smoothly to give the corresponding 1,3-dipolar cycloadducts, fluorine-containing pyrrolidines, in good yields and with high diastereoselectivities (>95:<5). When the fluorinated acrylate bore a chiral auxiliary as a substituent, for instance ( l)-(-)-menthyl ester, the 1,3-dipolar cycloaddition reaction was found to give the corresponding fluorinated pyrrolidine derivatives in not only a diastereoselective but also an enantioselective manner.
- Subjects
STEREOSELECTIVE reactions; PYRROLIDINE derivatives; IMINO compounds; RING formation (Chemistry); ACRYLATES
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 26, p4561
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600837