10.1021/ol503441d.s001
David M. Hodgson
David M.
Hodgson
Claire
L. Mortimer
Claire
L.
Mortimer
Jeffrey
M. McKenna
Jeffrey
M.
McKenna
Amine Protection/α-Activation with the <i>tert</i>-Butoxythiocarbonyl Group: Application to Azetidine
Lithiation–Electrophilic Substitution
American Chemical Society
2015
adduct
electrophile incorporation
Application
analogue
Lithiation
thermolysi
chiral ligand
deprotection
Facile
Protection
lithiation
Botc
ethanol
Boc
TFA
Azetidine
Amine
thiocarbonyl
alkoxycarbonyl cousin
2015-12-17 06:59:40
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Amine_Protection_Activation_with_the_i_tert_i_Butoxythiocarbonyl_Group_Application_to_Azetidine_Lithiation_Electrophilic_Substitution/2047257
<i>tert</i>-Butoxythiocarbonyl (Botc), the long-neglected
thiocarbonyl analogue of Boc, facilitates (unlike its alkoxycarbonyl
cousin) α-lithiation and electrophile incorporation on <i>N</i>-Botc-azetidine. <i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-<i>endo</i>,<i>endo</i>-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 <i>N</i>-Boc systems intact, was achieved using either TFA or via
thermolysis in ethanol.