title: Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition.
abstract: 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 viabeta-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.
authors.affiliation: Department of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK. steve.davies@chem.ox.ac.uk
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: A Christopher
authors.initials: AC
authors.lastname: Garner
authors.forename: Euan C
authors.initials: EC
authors.lastname: Goddard
authors.forename: Dennis
authors.initials: D
authors.lastname: Kruchinin
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
authors.forename: Humberto
authors.initials: H
authors.lastname: Rodriguez-Solla
authors.forename: James E
authors.initials: JE
authors.lastname: Thomson
authors.forename: Steven M
authors.initials: SM
authors.lastname: Toms
mesh_terms: D000577:Amides / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D009942:Organometallic Compounds; D011759:Pyrrolidines; D008094:Lithium