1602864-52-7Relevant academic research and scientific papers
Trisubstituted 2-trifluoromethyl pyrrolidines via catalytic asymmetric michael addition/reductive cyclization
Corbett, Michael T.,Xu, Qihai,Johnson, Jeffrey S.
supporting information, p. 2362 - 2365 (2014/05/20)
The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asymmetric Michael addition/hydrogenative cyclization is described. The direct organocatalytic addition of 1,1,1-trifluoromethylketones to nitroolefins proceeds under mild reaction conditions and low catalyst loadings to provide Michael adducts in high yield with excellent diastereo- and enantioselectivity. Catalytic hydrogenation of the Michael adducts stereoselectively generates 2-trifluoromethylated pyrrolidines bearing three contiguous stereocenters. A stereospecific route to epimeric 2-trifluoromethyl pyrrolidines from a common intermediate is described.
