Premium
Nucleophile‐Directed Selective Transformation of cis ‐1‐Tosyl‐2‐tosyloxymethyl‐3‐(trifluoromethyl)aziridine into Aziridines, Azetidines, and Benzo‐Fused Dithianes, Oxathianes, Dioxanes, and (Thio)morpholines
Author(s) -
Kenis Sara,
D'hooghe Matthias,
Verniest Guido,
Reybroeck Maaike,
Dang Thi Tuyet Anh,
Pham The Chinh,
Thi Pham Tham,
Törnroos Karl W.,
Van Tuyen Nguyen,
De Kimpe Norbert
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204485
Subject(s) - aziridine , tosyl , trifluoromethyl , chemistry , nucleophile , thio , electrophile , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , ring (chemistry) , catalysis , alkyl
A five‐step procedure for the synthesis of cis ‐1‐tosyl‐2‐tosyloxymethyl‐3‐(trifluoromethyl)aziridine was developed, starting from 1‐ethoxy‐2,2,2‐trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N ‐, O ‐ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis ‐1‐tosyl‐2‐tosyloxymethyl‐3‐(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo‐fused dithianes, oxathianes, dioxanes, and (thio)morpholines.