title: Amine protection/α-activation with the tert-butoxythiocarbonyl group: application to azetidine lithiation-electrophilic substitution.
abstract: tert-Butoxythiocarbonyl (Botc), the long-neglected thiocarbonyl analogue of Boc, facilitates (unlike its alkoxycarbonyl cousin) α-lithiation and electrophile incorporation on N-Botc-azetidine. N,N,N',N'-endo,endo-Tetramethyl-2,5-diaminonorbornane proved optimal as a chiral ligand, generating adducts with er up to 92:8. Facile deprotection, under conditions that left the corresponding N-Boc systems intact, was achieved using either TFA or via thermolysis in ethanol.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford OX1 3TA, U.K.
authors.forename: David M
authors.initials: DM
authors.lastname: Hodgson
authors.forename: Claire L
authors.initials: CL
authors.lastname: Mortimer
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: McKenna
mesh_terms: D000588:Amines / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D005563:Formic Acid Esters / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D001384:Azetidines; D003959:Diamines; D005563:Formic Acid Esters; C000600333:N,N,N',N'-endo,endo-tetramethyl-2,5-diaminonorbornane; D009636:Norbornanes; D009942:Organometallic Compounds; C000345:t-butyloxycarbonyl group; C082735:azetidine; D008094:Lithium