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An Organocatalytic Synthesis of cis‐N ‐Alkyl‐ and N ‐Arylaziridine Carboxylates
Author(s) -
Bew Sean P.,
Carrington Rachel,
Hughes David L.,
Liddle John,
Pesce Paolo
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900474
Subject(s) - chemistry , alkyl , pyridinium , trifluoromethanesulfonate , aldehyde , organocatalysis , amine gas treating , organic chemistry , enantioselective synthesis , catalysis , optically active , combinatorial chemistry
An extremely mild protocol that employs readily available starting materials, i.e., aldehyde, amine and alkyl diazoacetate, returns structurally diverse N ‐substituted‐C‐2/3‐difunctionalised aziridines in excellent yields and stereoselectivities when pyridinium triflate is incorporated as an organocatalyst. The reaction process is environmentally benign affording water and nitrogen as the only by‐products. This racemic protocol paves the way for the development of novel asymmetric organocatalysts capable of generating optically active aziridines.