ol503441d_si_001.pdf (2.94 MB)
Amine Protection/α-Activation with the tert-Butoxythiocarbonyl Group: Application to Azetidine Lithiation–Electrophilic Substitution
journal contribution
posted on 2015-12-17, 06:59 authored by David M. Hodgson, Claire
L. Mortimer, Jeffrey
M. McKennatert-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.