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Diastereoselectively Switchable Asymmetric Haloaminocyclization for the Synthesis of Cyclic Sulfamates
Author(s) -
Cai Yunfei,
Zhou Pengfei,
Liu Xiaohua,
Zhao Jiannan,
Lin Lili,
Feng Xiaoming
Publication year - 2015
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.201500454
Subject(s) - yield (engineering) , catalysis , chemistry , halogen , combinatorial chemistry , enantioselective synthesis , medicinal chemistry , organic chemistry , materials science , alkyl , metallurgy
An asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N , N ′‐dioxides with Sc(OTf) 3 or Lu(OTf) 3 as the catalyst, a variety of enantioenriched syn ‐ and anti ‐cyclic sulfamates or related trans ‐aziridines could be obtained in 92–99 % ee and up to 97 % yield.