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Organocatalyzed Aziridination of α‐Branched Enals: Enantioselective Synthesis of Aziridines with a Quaternary Stereocenter
Author(s) -
Desmarchelier Alaric,
Pereira de Sant'Ana Danilo,
Terrasson Vincent,
Campagne Jean Marc,
Moreau Xavier,
Greck Christine,
Marcia de Figueiredo Renata
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100437
Subject(s) - chemistry , enantioselective synthesis , aziridine , aldehyde , alcohol , organocatalysis , trimethylsilyl , ring (chemistry) , organic chemistry , catalysis , conjugate , combinatorial chemistry , mathematical analysis , mathematics
Organocatalytic access to N ‐tosylaziridines catalyzed by diarylprolinol trimethylsilyl ether [Ar = 3,5‐(CF 3 ) 2 C 6 H 3 ] starting from different α‐substituted‐α,β‐unsaturated aldehydes is described. The products were obtained in good yields (up to 86 %) and enantioselectivities (up to 90 % ee ) and could rapidly be transformed under various conditions, including ring opening, to afford useful small molecules possessing not only the aziridine and aldehyde moieties but also other functionalities such as alcohol, acid, ester, or amino alcohol.