945483-28-3Relevant articles and documents
Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition
Davies, Stephen G.,Garner, A. Christopher,Goddard, Euan C.,Kruchinin, Dennis,Roberts, Paul M.,Smith, Andrew D.,Rodriguez-Solla, Humberto,Thomson, James E.,Toms, Steven M.
, p. 1961 - 1969 (2008/02/08)
The diastereoselective conjugate addition of homochiral lithium amides to methyl 4-(N-allyl-N-benzylamino)but-2-enoate has been used as the key step in a simple and efficient protocol for the preparation of 3,4-substituted aminopyrrolidines. This protocol provides a complementary and stereoselective route to both anti- and syn-3-amino-4-alkylpyrrolidines as well as anti- and syn-3-hydroxy-4-aminopyrrolidines, in high de and ee via β-amino enolate functionalisation. This methodology has been applied to the synthesis of anti-(3S,4S)- and syn-(3R,4S)-3-methoxy-4-(N-methylamino)pyrrolidine. The Royal Society of Chemistry.