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Amine Protection/α-Activation with the t-Butoxythiocarbonyl Group: Application to Azetidine Lithiation−Electrophilic Substitution

Mckenna, Jeffrey and Hodgson, David M and Mortimer, Claire L (2015) Amine Protection/α-Activation with the t-Butoxythiocarbonyl Group: Application to Azetidine Lithiation−Electrophilic Substitution. Org Lett.

Abstract

t-Butoxythiocarbonyl (Botc), the long-neglected thiocarbonyl analogue of Boc, facilitates
(unlike its alkoxycarbonyl cousin) α-lithiation and electrophile incorporation on N-Botcazetidine.
N,N,N',N'-endo,endo-tetramethyl-2,5-diaminonorbornane proved optimal as a
chiral ligand, generating adducts in up to 92:8 er. Facile deprotection, under conditions which
left the corresponding N-Boc systems intact, was achieved using either TFA, or via
thermolysis in ethanol.

Item Type: Article
Date Deposited: 26 Apr 2016 23:45
Last Modified: 26 Apr 2016 23:45
URI: https://oak.novartis.com/id/eprint/23174

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