%0 Generic
%A D'hooghe, Matthias
%A Vanlangendonck, Tim
%A Törnroos, Karl W.
%A Kimpe, Norbert De
%D 2006
%T Novel Synthesis of cis-3,5-Disubstituted
Morpholine Derivatives
%U https://acs.figshare.com/articles/dataset/Novel_Synthesis_of_i_cis_i_3_5_Disubstituted_Morpholine_Derivatives/3076549
%R 10.1021/jo060313y.s001
%2 https://acs.figshare.com/ndownloader/files/4782349
%K ci
%K time diastereoselectively
%K premised cyclization
%K Novel Synthesis
%K nucleophilic displacement
%K bromo atoms
%K latter morpholine
%K synthesis
%X 1-tert-Butyl-2-(allyloxymethyl)aziridine has been transformed for the first time diastereoselectively into cis-3,5-di(bromomethyl)-4-tert-butylmorpholine via an electrophile-induced ring closure using bromine in dichloromethane. The
latter morpholine has been used as a substrate for the
synthesis of the corresponding 3,5-di(methoxymethyl)morpholine and 3,5-di(cyanomethyl)morpholine upon nucleophilic displacement of both bromo atoms. Further evaluation
of this protocol toward the synthesis of 4-arylmethyl- and
4-alkylmethyl-3,5-di(bromomethyl)morpholines showed that
the premised cyclization of the corresponding 2-(allyloxymethyl)aziridines into 3,5-di(bromomethyl)morpholines only
proceeded well for the N-neopentylmorpholine, which was
subsequently transformed into a 3-oxa-7-thia-9-azabicyclo[3.3.1]nonane derivative. Also, in some other cases, the
desired 3,5-di(bromomethyl)morpholines were isolated in low
yields and transformed into the corresponding 3,5-di(cyanomethyl)morpholines.
%I ACS Publications